2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides

ABSTRACT

The invention relates to novel compounds of the formula (I) 
                         
in which the R 1 , R 2a , R 2b , R 3 , A 1 , A 2 , A 3 , A 4 , A 5  and n radicals are each as defined above,
 
to the use thereof as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for preparation thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a National Stage entry of International ApplicationNo. PCT/EP2015/052351, filed Feb. 5, 2015, which claims priority toEuropean Patent Application No. 14155372.7, filed Feb. 17, 2014. Thedisclosures of the priority applications are incorporated in theirentirety herein by reference.

BACKGROUND

Field of the Invention

The present invention relates to novel 2-(het)aryl-substituted fusedbicyclic heterocycle derivatives of the formula (I), to the use thereofas acaricides and/or insecticides for controlling animal pests,particularly arthropods and especially insects and arachnids, and toprocesses and intermediates for preparation thereof.

Description of Related Art

2-(Het)aryl-substituted fused bicyclic heterocycle derivatives havinginsecticidal properties have already been described in the literature,for example in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO2013/018928, WO 2014/142292 and WO 2014/148451, and also WO 2015/000715.

However, the active ingredients already known according to the documentscited above have some disadvantages on application, whether because theyexhibit only a narrow range of application or because they do not havesatisfactory insecticidal or acaricidal activity.

SUMMARY

Novel 2-(het)aryl-substituted fused bicyclic heterocycle derivativeshave now been found, and these have advantages over the compoundsalready known, examples of which are better biological or environmentalproperties, a wider range of application methods, better insecticidal oracaricidal activity, and also good compatibility with crop plants. The2-(het)aryl-substituted fused bicyclic heterocycle derivatives can beused in combination with further agents for improving efficacy,especially against insects that are difficult to control.

The present invention therefore provides novel compounds of the formula(I)

in which

-   A¹ is nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² is —N—R⁵, oxygen or sulphur,-   A³ is oxygen, ═N—H or ═N—CN,-   A⁴ is nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A⁵ is nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   R¹ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, amino, (C₁-C₆)alkylamino,    di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,    (C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonylamino,    aminosulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,    di(C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,    -   or is (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyl,        (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, each of which is mono- or        polysubstituted identically or differently by aryl, hetaryl or        heterocyclyl, where aryl, hetaryl or heterocyclyl may each        independently be mono- or polysubstituted identically or        differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,        carbamoyl, aminosulphonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy,        (C₁-C₆)alkylthio, (C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,        (C₁-C₆)alkylsulphimino, (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)alkylsulphoximino, (C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)alkoxycarbonyl, (C₁-C₆)alkylcarbonyl,        (C₃-C₆)trialkylsilyl or benzyl, or-   R¹ is aryl, hetaryl or heterocyclyl, each of which is mono- or    polysubstituted identically or differently by halogen, cyano, nitro,    hydroxyl, amino, carboxyl, carbamoyl, (C₁-C₆)alkyl,    (C₃-C₈)cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)haloalkyl,    (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)alkylsulphonyl, (C₁-C₆)alkylsulphimino,    (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl,    (C₁-C₆)alkylsulphoximino, (C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl,    (═O) (only in the case of heterocyclyl) or (═O)₂ (only in the case    of heterocyclyl),-   R^(2a), R^(2b), R³ and R⁴ are each independently hydrogen, cyano,    halogen, nitro, acetyl, hydroxyl, amino, SCN, tri-(C₁-C₆)alkylsilyl,    (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,    (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,    (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,    (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,    (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,    (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,    (C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alkylaminosulphonyl,    (C₁-C₆)alkylsulphoximino, aminothiocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₃-C₈)cycloalkylamino,    -   is aryl or hetaryl, each of which is mono- or polysubstituted        identically or differently, where (in the case of hetaryl) at        least one carbonyl group may optionally be present and/or where        possible substituents in each case are as follows: cyano,        carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,        tri-(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,        (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,        hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,        (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,        (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,        (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,        (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,        (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,        (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,        (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,        (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,        (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,        (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,        (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,        (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,        (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,        (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,        (C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alkylaminosulphonyl,        (C₁-C₆)alkylsulphoximino, aminothiocarbonyl,        (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,        (C₃-C₈)cycloalkylamino,-   R⁵ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or    (C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl,-   n is 0, 1 or 2,    -   where, in the case that n=2, the meanings of A³ may be the same        or different.

It has additionally been found that the compounds of the formula (I)have very good efficacy as pesticides, preferably as insecticides and/oracaricides, and additionally generally have very good plantcompatibility, especially with respect to crop plants.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The inventive compounds are defined in general terms by the formula (I).Preferred substituents or ranges of the radicals given in the formulaementioned above and below are illustrated hereinafter:

-   A¹ is preferably nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² is preferably —N—R⁵, oxygen or sulphur,-   A³ is preferably oxygen, ═N—H or ═N—CN,-   A⁴ is preferably nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A⁵ is preferably nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   R¹ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,    (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    (C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonylamino,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonylamino,    -   or is (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₄)alkenyl,        (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl, each of which is optionally        mono- or disubstituted identically or differently by aryl,        hetaryl or heterocyclyl, where aryl, hetaryl and heterocyclyl        may each optionally be mono- or disubstituted identically or        differently by halogen, cyano, carbamoyl, aminosulphonyl,        (C₁-C₄)alkyl, (C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,        (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)alkylsulphimino, or-   R¹ is preferably aryl, hetaryl or heterocyclyl, each of which is    optionally mono- or disubstituted identically or differently by    halogen, cyano, carbamoyl, (C₁-C₄)alkyl, (C₃-C₆)cycloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,    (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)alkylsulphimino, (C₁-C₄)alkylsulphoximino,    (C₁-C₄)alkylcarbonyl, (C₃-C₄)trialkylsilyl, (═O) (only in the case    of heterocyclyl) or (═O)₂ (only in the case of heterocyclyl),-   R^(2a), R^(2b), R³ and R⁴ are preferably each independently    hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri-(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,    (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkylhydroxyimino,    (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,    di(C₁-C₄)alkylaminosulphonyl, aminothiocarbonyl,    -   is phenyl or hetaryl, each of which is mono- or disubstituted        identically or differently, where (in the case of hetaryl) at        least one carbonyl group may optionally be present and/or where        possible substituents in each case are as follows: cyano,        halogen, nitro, acetyl, amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,        (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,        (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,        (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,        (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,        (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,        (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,        di(C₁-C₄)alkylaminosulphonyl,-   R⁵ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,    (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   n is preferably 0, 1 or 2,    -   where, in the case that n=2, the meanings of A³ may be the same        or different.-   A¹ is more preferably nitrogen or ═C—R⁴,-   A² is more preferably —N—R⁵ or oxygen,-   A³ is more preferably oxygen or ═N—H,-   A⁴ is more preferably nitrogen or ═C—R⁴,-   A⁵ is more preferably nitrogen or ═C—R⁴,-   R¹ is more preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    -   or is (C₁-C₄)alkyl optionally monosubstituted by phenyl,        pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl,        triazolyl, thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl        or oxetanyl, where phenyl, pyridyl, pyrimidyl, pyridazinyl,        pyrazinyl, pyrazolyl, triazolyl, thiazolyl, tetrazolyl,        piperazinyl, tetrahydrofuryl or oxetanyl may each optionally be        mono- or disubstituted identically or differently by halogen,        (C₁-C₄)alkyl or (C₁-C₄)haloalkyl, or-   R¹ is more preferably phenyl, pyridyl, pyrimidyl, pyridazinyl,    pyrazinyl, pyrazolyl, triazolyl, thiazolyl, tetrazolyl, piperazinyl,    tetrahydrofuryl or oxetanyl, each of which is optionally mono- or    disubstituted identically or differently by halogen, (C₁-C₄)alkyl or    (C₁-C₄)haloalkyl,-   R^(2a) is more preferably hydrogen, halogen, (C₁-C₄)alkyl    (C₁-C₄)haloalkyl, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylthio,    (C₁-C₄)haloalkylsulphinyl or (C₁-C₄)haloalkylsulphonyl,-   R^(2b) is more preferably hydrogen or halogen,-   R³ is more preferably hydrogen, (C₁-C₄)alkyl (C₁-C₄)haloalkyl,    (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulphinyl or    (C₁-C₄)haloalkylsulphonyl,-   R⁴ is more preferably hydrogen, halogen, cyano or (C₁-C₃)alkyl,-   R⁵ is more preferably (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,-   n is more preferably 0, 1 or 2,    -   where, in the case that n=2, the meanings of A³ may be the same        or different.-   A¹ is even more preferably nitrogen or ═C—R⁴,-   A² is even more preferably —N—R⁵ or oxygen,-   A³ is even more preferably oxygen,-   A⁴ is even more preferably nitrogen or ═C—H,-   A⁵ is even more preferably nitrogen or ═C—H,-   R¹ is even more preferably methyl, ethyl, n-propyl, i-propyl,    cyclopropyl, n-butyl, i-butyl, tert-butyl, cyclobutyl, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,    trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, —(CH₂)₂—S—C₂H₅,    —(CH₂)₂—SO₂—C₂H₅ or

-   R^(2a) is even more preferably hydrogen, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,    trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethylthio, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, fluorine or chlorine,-   R^(2b) is even more preferably hydrogen, fluorine or chlorine,-   R³ is even more preferably fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl, pentafluoroethyl, trifluoromethylthio,    trifluoromethylsulphonyl or trifluoromethylsulphinyl,-   R⁴ is even more preferably hydrogen, fluorine, chlorine, bromine or    cyano,-   R⁵ is even more preferably methyl, ethyl, i-propyl, methoxymethyl or    methoxyethyl,-   n is even more preferably 0, 1 or 2.-   A¹ is specifically nitrogen (N) or ═C—H,-   A² is specifically —N—CH₃ or oxygen (O),-   A³ is specifically oxygen (O),-   A⁴ is specifically nitrogen (N) or ═C—H,-   A⁵ is specifically ═C—H,-   R¹ is specifically methyl, ethyl, n-propyl, i-propyl,    trifluoromethyl, —(CH₂)₂—S—C₂H₅, —(CH₂)₂—SO₂—C₂H₅ or

-   R^(2a) is specifically hydrogen, trifluoromethyl, fluorine or    chlorine,-   R^(2b) is specifically hydrogen or chlorine,-   R³ is specifically trifluoromethyl,-   n is specifically 0, 1 or 2.

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-A)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-B)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-C)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-D)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-E)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-F)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-G)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-H)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-I)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-J)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-K)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-L)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-M)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-N)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-O)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-P)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-Q)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-R)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-S)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-T)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-U)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-V)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-W)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-X)

In the formulae (I-A) to (I-X), the R¹, R^(2a), R^(2b), R³, A¹, A², A³,A⁴, A⁵ and n radicals are each as defined above.

In a further embodiment (Configuration 1), the invention relates tocompounds of the formula (I)

in which

-   A¹ is nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² is —N—R⁵, oxygen or sulphur,-   A³ is oxygen,-   A⁴ is nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A⁵ is ═C—H,-   R¹ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, amino, (C₁-C₆)alkylamino,    di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,    (C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonylamino,    aminosulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,    di(C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,    -   or is in each case identically or differently optionally mono-        or poly-aryl-, -hetaryl- or -heterocyclyl-substituted        (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,        (C₃-C₈)cycloalkyl, where aryl, hetaryl or heterocyclyl may each        independently be mono- or polysubstituted identically or        differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,        carbamoyl, aminosulphonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy,        (C₁-C₆)alkylthio, (C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,        (C₁-C₆)alkylsulphimino, (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)alkylsulphoximino, (C₁-C₆)alky        lsulphoximino-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphoximino-(C₂-C₆)alky        lcarbonyl, (C₁-C₆)alkoxycarbonyl, (C₁-C₆)alkylcarbonyl,        (C₃-C₆)trialkylsilyl or benzyl, or-   R¹ is aryl, hetaryl or heterocyclyl, each of which is optionally    mono- or polysubstituted identically or differently by halogen,    cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, (C₁-C₆)alkyl,    (C₃-C₈)cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)haloalkyl,    (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)alkylsulphonyl, (C₁-C₆)alkylsulphimino,    (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl,    (C₁-C₆)alkylsulphoximino, (C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl,    (═O) (only in the case of heterocyclyl) or (═O)₂ (only in the case    of heterocyclyl),-   R^(2a), R^(2b), R³ and R⁴ are each independently hydrogen, cyano,    halogen, nitro, acetyl, hydroxyl, amino, SCN, tri-(C₁-C₆)alkylsilyl,    (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,    (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,    (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,    (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,    (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,    (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alky lcarbonyloxy,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,    (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,    (C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alkylaminosulphonyl,    (C₁-C₆)alkylsulphoximino, aminothiocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl    ((C₁-C₆)alkylcarbonylamino),    -   is aryl or hetaryl, each of which is optionally mono- or        polysubstituted identically or differently, where (in the case        of hetaryl) at least one carbonyl group may optionally be        present and/or where possible substituents in each case are as        follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl,        amino, SCN, tri-(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl,        (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,        hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,        (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,        (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,        (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,        (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,        (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,        (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,        (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,        (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,        (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,        (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,        (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,        (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,        (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,        (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,        (C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alky laminosulphonyl,        (C₁-C₆)alkylsulphoximino, aminothiocarbonyl,        (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,        (C₃-C₈)cycloalkylamino,-   R⁵ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or    (C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl,-   n is 0, 1 or 2.

Preference (Configuration 2) is given to compounds of the formula (I) inwhich

-   A¹ is nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² is —N—R⁵, oxygen or sulphur,-   A³ is oxygen,-   A⁴ is nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A⁵ is ═C—H,-   R¹ is (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    (C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonylamino,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonylamino,    -   or is (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₄)alkenyl,        (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl, each of which is optionally        mono- or disubstituted identically or differently by aryl,        hetaryl or heterocyclyl, where aryl, hetaryl and heterocyclyl        may each optionally be mono- or disubstituted identically or        differently by halogen, cyano, carbamoyl, aminosulphonyl,        (C₁-C₄)alkyl, (C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,        (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)alkylsulphimino, or-   R¹ is aryl, hetaryl or heterocyclyl, each of which is optionally    mono- or disubstituted identically or differently by halogen, cyano,    carbamoyl, (C₁-C₄)alkyl, (C₃-C₆)cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,    (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)alkylsulphimino, (C₁-C₄)alkylsulphoximino,    (C₁-C₄)alkylcarbonyl, (C₃-C₄)trialkylsilyl, (═O) (only in the case    of heterocyclyl) or (═O)₂ (only in the case of heterocyclyl),-   R^(2a), R^(2b), R³ and R⁴ are each independently hydrogen, cyano,    halogen, nitro, acetyl, hydroxyl, amino, SCN, tri-(C₁-C₄)alkylsilyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,    (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,    di(C₁-C₄)alkylaminosulphonyl, aminothiocarbonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino),    -   is phenyl or hetaryl, each of which is mono- or disubstituted        identically or differently, where (in the case of hetaryl) at        least one carbonyl group may optionally be present and/or where        possible substituents in each case are as follows: cyano,        halogen, nitro, acetyl, amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,        (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,        (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,        (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,        (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,        (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,        (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,        (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,        (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino,        di(C₁-C₄)alkylamino, aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,        di(C₁-C₄)alkylaminosulphonyl,-   R⁵ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,    (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   n is 0, 1 or 2.

Particular preference (Configuration 3) is given to compounds of theformula (I) in which

-   A¹ is nitrogen or ═C—R⁴,-   A² is —N—R⁵ or oxygen,-   A³ is oxygen,-   A⁴ is nitrogen or ═C—R⁴,-   A⁵ is ═C—H,-   R¹ is (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    -   or is (C₁-C₄)alkyl optionally monosubstituted by phenyl,        pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl,        triazolyl, thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl        or oxetanyl, where phenyl, pyridyl, pyrimidyl, pyridazinyl,        pyrazinyl, pyrazolyl, triazolyl, thiazolyl, tetrazolyl,        piperazinyl, tetrahydrofuryl or oxetanyl may each optionally be        mono- or disubstituted identically or differently by halogen,        (C₁-C₄)alkyl or (C₁-C₄)haloalkyl, or-   R¹ is phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl,    triazolyl, thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or    oxetanyl, each of which is optionally mono- or disubstituted    identically or differently by halogen, (C₁-C₄)alkyl or    (C₁-C₄)haloalkyl,-   R^(2a) is hydrogen, cyano, aminocarbonyl, halogen, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,    (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylthio,    (C₁-C₄)haloalkylsulphinyl or (C₁-C₄)haloalkylsulphonyl,-   R^(2b) is hydrogen, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,    NHCO—(C₁-C₄)alkyl or halogen,-   R³ is hydrogen, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylthio,    (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)haloalkylsulphonyl, or is phenyl,    pyrazolyl or imidazolyl, each of which is optionally monosubstituted    by trifluoromethyl,-   R⁴ is hydrogen, halogen, cyano or (C₁-C₃)alkyl,-   R⁵ is (C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl,-   n is 0, 1 or 2.

Very particular preference (Configuration 4) is given to compounds ofthe formula (I) in which

-   A¹ is nitrogen or ═C—R⁴,-   A² is —N—R⁵ or oxygen,-   A³ is oxygen,-   A⁴ is nitrogen or ═C—H,-   A⁵ is ═C—H,-   R¹ is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl,    i-butyl, tert-butyl, cyclobutyl, hydroxyethyl (—CH₂—CH₂—OH),    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    —(CH₂)₂—S—C₂H₅, —(CH₂)₂—SO₂—C₂H₅ or

-   R^(2a) is hydrogen, cyano, aminocarbonyl (CONH₂), fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,    trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,    trifluoromethylthio, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, fluorine or chlorine,-   R^(2b) is hydrogen, methoxy, ethoxy, trifluoromethyl,    methylcarbonylamino (NHCO-methyl), fluorine or chlorine,-   R³ is fluorine, chlorine, fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,    difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio,    trifluoromethylsulphonyl, trifluoromethylsulphinyl, or is phenyl,    pyrazol-1-yl or imidazol-1-yl, each of which is optionally    monosubstituted by trifluoromethyl,-   R⁴ is hydrogen, fluorine, chlorine, bromine or cyano,-   R⁵ is methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,-   n is 0, 1 or 2.

Emphasis (Configuration 5) is given to compounds of the formula (I) inwhich

-   A¹ is nitrogen (N) or ═C—H,-   A² is —N—CH₃ or oxygen (O),-   A³ is oxygen (O),-   A⁴ is nitrogen (N) or ═C—H,-   A⁵ is ═C—H,-   R¹ is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl,    i-butyl, tert-butyl, cyclobutyl, hydroxyethyl (—CH₂—CH₂—OH),    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    —(CH₂)₂—S—C₂H₅, —(CH₂)₂—SO₂—C₂H₅ or

(oxetan-3-yl),

-   R^(2a) is hydrogen, cyano, aminocarbonyl (CONH₂), fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,    trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, fluorine or chlorine,-   R^(2b) is hydrogen, methoxy, ethoxy, trifluoromethyl,    methylcarbonylamino (NHCO-methyl), fluorine or chlorine,-   R³ is fluorine, chlorine, fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,    trifluoromethylthio, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, or is phenyl,

(pyrazol-1-yl) or

(imidazol-1-yl), each of which is optionally monosubstituted bytrifluoromethyl,

-   n is 0, 1 or 2.

Particular emphasis (Configuration 6) is given to compounds of theformula (I) in which

-   A¹ is nitrogen (N) or ═C—H,-   A² is —N—CH₃ or oxygen (O),-   A³ is oxygen (O),-   A⁴ is nitrogen (N) or ═C—H,-   A⁵ is ═C—H,-   R¹ is methyl, ethyl, n-propyl, i-propyl, trifluoromethyl,    —CH₂—CH₂—F, —CH₂—CH₂—OH, —(CH₂)₂—S—C₂H₅, —(CH₂)₂—SO₂—C₂H₅ or

-   R^(2a) is hydrogen, trifluoromethyl, cyano, CONH₂, fluorine or    chlorine,-   R^(2b) is hydrogen, chlorine, trifluoromethyl, methoxy or NHCOCH₃,-   R³ is pentafluoroethyl, trifluoromethyl, chlorine, 4-CF₃(C₆H₄),    4-(CF₃)pyrazol-1-yl, 3-(CF₃)pyrazol-1-yl or 4-(CF₃)imidazol-1-yl,-   n is 0, 1 or 2.

In a further preferred embodiment, the invention relates to thecompounds of the formula (I) where R¹, R^(2a), R³, A¹, A², A³, A⁴, A⁵and n are each as defined above, especially as defined in Configuration(1) or Configuration (2) or Configuration (3) or Configuration (4) orConfiguration (5) or Configuration (6), and

-   R^(2b) is acetyl, amino, SCN, tri-(C₁-C₆)alkylsilyl,    (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,    (C₁-C₆)alkyl(C₃-C₈)cycloalkyl (where the bond is via the cycloalkyl    substituted by alkyl), halo(C₃-C₈)cycloalkyl, (C₂-C₆)alkenyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,    (C₁-C₆)haloalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylsulphinyl, (C₁-C₆)haloalkylsulphinyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,    (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,    (C₁-C₆)alkylsulphonyloxy, (C₁-C₆)alkylcarbonyl,    (C₁-C₆)alkylthiocarbonyl, (C₁-C₆)haloalkylcarbonyl,    (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,    (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)alkylaminocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,    di-(C₁-C₆)alkylaminothiocarbonyl, (C₂-C₆)alkenylaminocarbonyl,    di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)cycloalkylaminocarbonyl,    (C₁-C₆)alkylsulphonylamino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino,    aminosulphonyl, (C₁-C₆)alkylaminosulphonyl,    di-(C₁-C₆)alkylaminosulphonyl, (C₁-C₆)alkylsulphoximino,    aminothiocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di-(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylamino,    NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino),    -   is in each case optionally singly or multiply, identically or        differently substituted hetaryl, where at least one carbonyl        group may optionally be present and/or where possible        substituents in each case are as follows: cyano, carboxyl,        halogen, nitro, acetyl, hydroxyl, amino, SCN,        tri-(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,        (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,        hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,        (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,        (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,        (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,        (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,        (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,        (C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,        (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,        (C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,        (C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,        (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,        (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,        (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,        (C₂-C₆)alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,        (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulphonyl,        (C₁-C₆)alkylaminosulphonyl, di-(C₁-C₆)alky laminosulphonyl,        (C₁-C₆)alkylsulphoximino, aminothiocarbonyl,        (C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,        (C₃-C₈)cycloalkylamino.

In a further preferred embodiment, the invention relates to thecompounds of the formula (I) where R¹, R^(2a), R³, A¹, A², A³, A⁴, A⁵and n are each as defined above, especially as defined in Configuration(1) or Configuration (2) or Configuration (3) or Configuration (4) orConfiguration (5) or Configuration (6), and

-   R^(2b) is acetyl, amino, SCN, tri-(C₁-C₄)alkylsilyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl(C₃-C₆)cycloalkyl (where the bond is via the cycloalkyl    substituted by alkyl), halo(C₃-C₆)cycloalkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,    (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,    (C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,    (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,    aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,    di-(C₁-C₄)alkylaminosulphonyl, aminothiocarbonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino), is in each case singly or doubly,    identically or differently substituted hetaryl, where at least one    carbonyl group may optionally be present and/or where possible    substituents in each case are as follows: cyano, halogen, nitro,    acetyl, amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,    (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,    (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,    (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,    (C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,    di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,    (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulphonyl,    (C₁-C₄)alkylaminosulphonyl, di-(C₁-C₄)alkylaminosulphonyl.

In a further preferred embodiment, the invention relates to thecompounds of the formula (I) where R¹, R^(2a), R³, A¹, A², A³, A⁴, A⁵and n are each as defined above, especially as defined in Configuration(1) or Configuration (2) or Configuration (3) or Configuration (4) orConfiguration (5) or Configuration (6), and R^(2b) is (C₁-C₄)alkoxy orNHCO—(C₁-C₄)alkyl.

In a further preferred embodiment, the invention relates to thecompounds of the formula (I) where R¹, R^(2a), R³, A¹, A², A³, A⁴, A⁵and n are each as defined above, especially as defined in Configuration(1) or Configuration (2) or Configuration (3) or Configuration (4) orConfiguration (5) or Configuration (6), and R^(2b) is methoxy, ethoxy orNHCO-methyl.

In a further preferred embodiment, the invention relates to thecompounds of the formula (I) where R¹, R^(2a), R³, A¹, A², A³, A⁴, A⁵and n are each as defined above, especially as defined in Configuration(1) or Configuration (2) or Configuration (3) or Configuration (4) orConfiguration (5) or Configuration (6), and R^(2b) is methoxy orNHCO-methyl.

R^(2b) is joined in the 3 or 5 position:

In the preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, naphthyl, anthryl, phenanthrenyl, andis preferably in turn phenyl,

hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group of furyl, thienyl,pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl,pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl,1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl,benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl,benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl,benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl,cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl and indolizinyl,

heterocyclyl is a saturated 4-, 5- or 6-membered ring containing 1 or 2nitrogen atoms and/or one oxygen atom and/or one sulphur atom, forexample azetidinyl, pyrrolidinyl, piperidinyl, oxetanyl,tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, thietanyl,tetrahydrothiophenyl, tetrahydrothiopyranyl, piperazinyl, morpholinyland thiomorpholinyl.

In the particularly preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, naphthyl, anthryl, phenanthrenyl, andis preferably in turn phenyl,

hetaryl (including as part of a larger unit, for example hetarylalkyl)is selected from the group of pyridyl, pyrimidyl, pyrazinyl,pyridazinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl and tetrazolyl,

heterocyclyl is selected from the group of oxetanyl, tetrahydrofuryl andpiperazinyl.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. From amongthese alkyl radicals, particular preference is given to C₁-C₆-alkylradicals. Special preference is given to C₁-C₄-alkyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl. Among these, preference is given to C₂-C₆-alkenylradicals and particular preference to C₂-C₄-alkenyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl. Among these, preference is given toC₃-C₆-alkynyl radicals and particular preference to C₃-C₄-alkynylradicals. The alkynyl radical may also contain at least one double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl. Among these, preference is given to C₃-C₆-cycloalkylradicals.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood to mean an O-alkyl radical,where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms can be identical ordifferent. In this case, halogen is fluorine, chlorine, bromine oriodine, especially fluorine, chlorine or bromine.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionmay be the same or different.

The radical definitions or elucidations given above in general terms orwithin areas of preference apply to the end products and correspondinglyto the starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective preferred ranges.

Preference is given in accordance with the invention to using compoundsof the formula (I) where a combination of the definitions listed aboveas preferred is present.

Particular preference is given in accordance with the invention to usingcompounds of the formula (I) where a combination of the definitionslisted above as particularly preferred is present.

Very particular preference is given in accordance with the invention tousing compounds of the formula (I) where a combination of thedefinitions listed above as very particularly preferred is present.

Emphasis is given in accordance with the invention to using compounds ofthe formula (I) where a combination of the definitions listed above asspecific is present.

Particular emphasis is given in accordance with the invention to usingcompounds of the formula (I) where a combination of the definitionslisted above as very specific is present.

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention thus encompasses purestereoisomers and any desired mixtures of these isomers.

The inventive compounds of the formula (I) can be obtained by theprocesses shown in the following schemes:

Process A

The R¹, R^(2a), R^(2b), R³, A¹, A², A³, A⁴, A⁵ and n radicals are eachas defined above.

Step a)

The compounds of the formula (IV) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with carboxylic acids of the formula (III)in the presence of a condensing agent.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257 or WO2006/65703.

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234604, WO2012/61926 or Bioorganic andMedicinal Chemistry Letters, 18 (2008), 5023-5026.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (III) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, forexample pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0 to 180° C.,preference being given to effecting the reaction at standard pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (I) can be prepared by condensing thecompounds of the formula (IV), for example analogously to the processesdescribed in WO2012/86848.

The conversion to compounds of the formula (I) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from the customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be conducted in the presence of a condensing agent, anacid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulphonic acids such as para-toluenesulphonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Process B

The R¹, R^(2a), R^(2b), R³, A¹, A², A, A⁴, A⁵ and n radicals are each asdefined above.

Step a)

In a further embodiment of the invention, compounds of the formula (IV)can be prepared by the reaction of compounds of the formula (II) withcarbonyl chlorides of the formula (V) in the presence of a condensingagent.

Carbonyl chlorides of the formula (V) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234603 or US2010/234604.

The reaction of the compounds of the formula (II) with carbonylchlorides of the formula (V) can be effected neat or in a solvent,preference being given to conducting the reaction in a solvent selectedfrom customary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; aliphatichydrocarbons such as hexane, heptane or octane; aromatic hydrocarbons,for example toluene or xylene; nitriles, for example acetonitrile orpropionitrile; aprotic polar solvents, for example N,N-dimethylformamideor N-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction is preferably effected in the presence of a base. Suitablebases of the inorganic bases which are typically used in such reactions.Preference is given to using bases selected by way of example from thegroup consisting of acetates, phosphates, carbonyl cates andhydrogencarbonates of alkali metals or alcustomaline earth metals.Particular preference is given to sodium acetate, sodium phosphate,potassium alkaline earth metals. Particular preference is given tosodium acetate, sodium phosphate, potassium phosphate, caesiumcarbonate, sodium carbonate, potassium carbonate, sodiumhydrogencarbonate, potassium hydrogencarbonate. Further suitable basesare tertiary amines such as triethylamine and N,N-diisopropylethylamine,and nitrogen heterocycles such as pyridine, picoline, 2,6-lutidine,4-dimethylaminopyridine and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU).

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of −20° C. to100° C., preference being given to effecting the reaction at standardpressure and temperatures of 0° C. to 80° C.

Step b)

The further conversion of the compounds of the formula (IV) to compoundsof the formula (I) is effected as in process A, step b).

Process C

The R¹, R^(2a), R^(2b), R³, A¹, A², A³, A⁴, A⁵ and n radicals are eachas defined above.

In a further embodiment of the invention, compounds of the formula (I)can be prepared in a one-stage process from the intermediate compoundsof the formulae (II) and (III) in the presence of a condensing agent.

The conversion to compounds of the formula (I) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from the customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol, ethanolor isopropanol; nitriles, for example acetonitrile or propionitrile;aromatic hydrocarbons, for example toluene or xylene; aprotic polarsolvents, for example N,N-dimethylformamide or N-methylpyrrolidone, ornitrogen compounds, for example pyridine.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

The reaction can be conducted in the presence of an acid or a base.

Examples of an acid which can be used in the reaction described aresulphonic acids such as methanesulphonic acid or para-toluenesulphonicacid; carboxylic acids such as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

The reaction can be conducted in the presence of a suitable catalyst,for example 1-hydroxybenzotriazole.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Process D

The R¹, R^(2a), R^(2b), R³, A¹, A², A³, A⁴, A⁵ and n radicals are eachas defined above.

In a further embodiment of the invention, compounds of the formula (I)can be prepared in a one-stage process from the intermediate compoundsof the formulae (II) and (V).

The conversion to compounds of the formula (I) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from the customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol, ethanolor isopropanol; nitriles, for example acetonitrile or propionitrile;aromatic hydrocarbons, for example toluene or xylene; aprotic polarsolvents, for example N,N-dimethylformamide or N-methylpyrrolidone, ornitrogen compounds, for example pyridine.

The reaction is preferably effected in the presence of a base. Suitablebases are inorganic bases which are typically used in such reactions.Preference is given to using bases selected by way of example from thegroup consisting of acetates, phosphates, hydroxides, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Preferenceis given to caesium carbonate, sodium carbonate, potassium carbonate,sodium hydroxide and potassium hydroxide. Further suitable bases aretertiary amines such as triethylamine and N,N-diisopropylethylamine,nitrogen heterocycles such as pyridine, picoline, 2,6-lutidine,4-dimethylaminopyridine and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU).

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Process E

The R¹, R^(2a), R^(2b), R³, A¹, A², A³, A⁴, A⁵ and n radicals are eachas defined above.

In a further embodiment of the invention, compounds of the formula (I)can be prepared from the compounds of the formula (II) and the aldehydesof the formula (VI) in the presence of an oxidizing agent.

Aldehydes of the formula (VI) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2009/192195, US2010/227894 or Angewandte Chemie,International Edition, 48 (2009), 7064-7068.

The conversion to compounds of the formula (I) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent. Preference is given to ethers, for example diisopropyl ether,dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether;halogenated hydrocarbons, for example dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols suchas methanol, ethanol or isopropanol; esters such as ethyl acetate;nitriles, for example acetonitrile or propionitrile; aromatichydrocarbons, for example toluene or xylene; aprotic polar solvents, forexample N,N-dimethylformamide or N-methylpyrrolidone, or nitrogencompounds, for example pyridine.

The reaction can be conducted in the presence of an acid. Examples ofacids which can be used in the reaction described are sulphonic acidssuch as methanesulphonic acid or para-toluenesulphonic acid; carboxylicacids such as acetic acid, or polyphosphoric acids.

The reaction can also be conducted in the presence of a sulphite.Examples of sulphites which can be used in the reaction described aresodium hydrogensulphite or sodium sulphite.

Examples of oxidizing agents which find use in the reaction describedare oxygen, copper(II) chloride or DDQ.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0 to 200° C.,preference being given to effecting the reaction at standard pressureand temperatures of 20 to 150° C.

Process F

The R¹, R^(2a), R^(2b), R³, A¹, A², A³, A⁴, A⁵ and n radicals are eachas defined above, and X¹ is halogen.

Step a)

The compounds of the formula (VIII) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with a carboxylic acid of the formula(VIIa) or with a carbonyl chloride of the formula (VIIb) in the presenceof a condensing agent or a base.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257 or WO2006/65703.

Carboxylic acids of the formula (VIIa) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234604, WO2012/61926 or Bioorganic andMedicinal Chemistry Letters, 18 (2008), 5023-5026.

Carbonyl chlorides of the formula (VIIb) are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in US2010/234603 or US2010/234604.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (VIIa) or carbonyl chlorides of the formula (VIIb) can beeffected neat or in a solvent, preference being given to conducting thereaction in a solvent selected from customary solvents that are inertunder the prevailing reaction conditions. Preference is given to ethers,for example diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane; halogenated hydrocarbons, for exampledichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene; nitriles, for example acetonitrile or propionitrile;aromatic hydrocarbons, for example toluene or xylene; aprotic polarsolvents, for example N,N-dimethylformamide or N-methylpyrrolidone, ornitrogen compounds, for example pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0 to 180° C.,preference being given to effecting the reaction at standard pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (IX) can be prepared by condensing theintermediate compounds of the formula (VIII), for example analogously tothe processes described in WO2012/86848.

The conversion to compounds of the formula (IX) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be conducted in the presence of a condensing agent, anacid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulphonic acids such as para-toluenesulphonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (I) where n is 0 can be prepared byreacting the intermediate compounds of the formula (IX) with theintermediate compounds of the formula (X) in the presence of a base.

Mercaptan derivatives of the formula (X), for example methyl mercaptan,ethyl mercaptan or isopropyl mercaptan, are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in US2006/25633, US2006/111591, U.S. Pat. No.2,820,062, Chemical Communications, 13 (2000), 1163-1164 or Journal ofthe American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formula (I) where n is 0 can beeffected neat or in a solvent, preference being given to conducting thereaction in a solvent selected from the customary solvents that areinert under the prevailing reaction conditions. Preference is given toethers, for example diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given to caesium carbonate, sodium carbonateand potassium carbonate. Further suitable bases are alkali metalhydrides, for example sodium hydride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

In the reaction described, X¹ is preferably a fluorine or chlorine atom.

Step d)

The compounds of the formula (I) where A³ is oxygen and n is 1 can beprepared by oxidizing the compounds of the formula (I) where n is 0. Theoxidation is generally conducted in a solvent selected from customarysolvents which are inert under the prevailing reaction conditions.Preference is given to halogenated hydrocarbons, for exampledichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene; alcohols such as methanol or ethanol; formic acid, aceticacid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step e)

The compounds of the formula (I) where A³ is oxygen and n is 2 can beprepared by oxidizing the compounds of the formula (I) where A³ isoxygen and n is 1. The oxidation is generally conducted in a solvent.Preference is given to halogenated hydrocarbons, for exampledichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene; alcohols such as methanol or ethanol; formic acid, aceticacid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step f)

The compounds of the formula (I) where A³ is oxygen and n is 2 can alsobe prepared in a one-stage process by oxidizing the compounds of theformula (I) where n is 0. The oxidation is generally conducted in asolvent. Preference is given to halogenated hydrocarbons, for exampledichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene; alcohols such as methanol or ethanol; formic acid, aceticacid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Process G

Compounds of the formula (I) for which R³=halogen can be converted toother compounds of the formula (I) for which R³ is another radicalaccording to the definition.

Compounds of the formula (I) for which R³ is a C-bonded radical from thegroup of aryl or heteroaryl according to the definition can be prepared,for example, from compounds of the formula (I) for which R³ ispreferably halogen from the group of chlorine or bromine by commonlyknown methods (cf. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58,9633-9695; Metal-Catalyzed Cross-Coupling Reactions (eds.: A. deMeijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004).

For example, compounds in which R³ is preferably chlorine or bromine canbe reacted with suitable arylboronic acids or esters thereof by knownmethods (cf. WO2010071819) in the presence of suitable catalysts fromthe group of the transition metal salts to give compounds of the formula(I) in which R³ is a radical from the group of aryl. Examples ofpreferred coupling catalysts include palladium catalysts such as[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) ortetrakis(triphenylphosphine)palladium. Suitable basic reactionauxiliaries used to conduct the processes are preferably carbonates ofsodium or potassium.

Some of the (hetero)arylboronic acids or (hetero)arylboronic estersrequired are known and/or commercially available, for example preparedby commonly known methods (cf. Boronic Acids (eds.: D. G. Hall), 2nded., Wiley-VCH, Weinheim, 2011).

The preparation of compounds of the formula (I) in which R³ is anN-bonded hetaryl, for example imidazol-1-yl and pyrazol-1-yl can beeffected by methods known from the literature (see, for example, Journalof Organic Chemistry (2010), 69, 5578), preferably in the presence ofcopper(I) iodide and basic reaction auxiliaries, for exampletrans-N,N′-dimethylcyclohexane-1,2-diamine and potassium carbonate, in asuitable solvent or diluent. Useful solvents or diluents include allinert organic solvents, for example aliphatic or aromatic hydrocarbons.Preference is given to using toluene.

Some of the compounds of the formula (II) are novel.

Novel compounds are those of the formula (IIa)

in which R³ is as defined above, though R³ must not be chlorine, bromineor CHO.

The present invention also provides compounds of the formula (IIa) inwhich R³ is (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)haloalkylthio,(C₁-C₄)haloalkylsulphinyl or (C₁-C₄)haloalkylsulphonyl, where R³ is notCF₃ or CHF₂.

Preferably, R³ is CH₂F, C₂H₄F, C₂H₃F₂, C₂H₂F₃, C₂HF₄, C₂F₅, n-C₃F₇,i-C₃F₇, OCH₂F, SCH₂F, SOCH₂F, SO₂CH₂F, OCHF₂, SCHF₂, SOCHF₂, SO₂CHF₂,OCF₃, OCF₂Cl, OCFCl₂, SCF₃, SOCF₃, SO₂CF₃, OC₂H₄F, SC₂H₄F, SOC₂H₄F,SO₂C₂H₄F, OC₂H₃F₂, SC₂H₃F₂, SOC₂H₃F₂, SO₂C₂H₃F₂, OC₂H₂F₃, SC₂H₂F₃,SOC₂H₂F₃, SO₂C₂H₂F₃, OC₂HF₄, SC₂HF₄, SOC₂HF₄, SO₂C₂HF₄, OC₂F₅, SC₂F₅,SOC₂F₅, SO₂C₂F₅, n-OC₃F₇, n-SC₃F₇, n-SOC₃F₇, n-SO₂C₃F₇, i-OC₃F₇,i-SC₃F₇, i-SOC₃F₇ or i-SO₂C₃F₇.

More preferably, R³ is CH₂F, OCF₃, C₂H₄F, C₂H₃F₂, C₂H₂F₃, C₂HF₄, C₂F₅,SCF₃, SOCF₃ or SO₂CF₃.

Most preferably, R³ is C₂F₅.

Process H

The R³ radical is as defined above.

Step a)

The compounds of the formula (XIII) can be prepared in analogy to theprocess described in WO2005/55928 or Journal of Medicinal Chemistry, 48(2005), p. 6128-6139, by the reaction of compounds of the formula (XI)with benzyl chlorocarbonate (benzyl chloroformate) of the formula (XII),for example in the presence of a base.

Compounds of the formula (XI) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in WO2012/3576, WO2007/47793 or WO2006/65703.

The conversion to compounds of the formula (XIII) can be effected insubstance or in a solvent, preference being given to conducting thereaction in a solvent selected from customary solvents that are inertunder the prevailing reaction conditions. Preference is given to ethers,for example diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile or aromatic hydrocarbons, for exampletoluene or xylene.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given to caesium carbonate, sodium carbonateand potassium carbonate.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to120° C.

Step b)

The compounds of the formula (IIa) can be prepared by reducing thecompounds of the formula (XIII), for example analogously to theprocesses described in Journal of Heterocyclic Chemistry, 22 (1985), p.313-318.

An example of a suitable reducing agent is lithium aluminium hydride.

The conversion to compounds of the formula (IIa) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane or tert-butyl methyl ether.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to100° C.

Also novel is the compound of the formula (II-02)

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablyconducted in agriculture and forestry, and in material protection.Preferably excluded from this are methods for the surgical ortherapeutic treatment of the human or animal body and diagnostic methodscarried out on the human or animal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection agents.

In the context of the present application, the term “pesticide” in eachcase also always comprises the term “crop protection agent”.

The compounds of the formula (I), given good plant tolerance, favourablehomeotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, nematodes and molluscs, which are encountered inagriculture, in horticulture, in animal husbandry, in aquatic cultures,in forests, in gardens and leisure facilities, in the protection ofstored products and of materials, and in the hygiene sector. They canpreferably be used as pesticides. They are effective against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., for example Acarus siro, Aceriakuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., for exampleBrevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., for example Eotetranychus hicoriae, Epitrimerus pyri,Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp.,for example Eriophyes pyri, Glycyphagus domesticus, Halotydeusdestructor, Hemitarsonemus spp., for example Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., for example Oligonychus coniferarum, Oligonychusilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychuspratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp.,Ornithonyssus spp., Panonychus spp., for example Panonychus citri(=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., for example Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., for example Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici; from the class of the Chilopoda, for example Geophilusspp., Scutigera spp.;

from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, for example Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp.,Periplaneta spp., for example Periplaneta americana, Periplanetaaustralasiae, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,for example Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., for example Anthonomus grandis, Anthrenus spp., Apionspp., Apogonia spp., Atomaria spp., for example Atomaria linearis,Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp.,for example Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotomatrifurcata, Ceutorrhynchus spp., for example Ceutorrhynchus assimilis,Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., forexample Chaetocnema confinis, Chaetocnema denticulata, Chaetocnemaectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., for exampleCosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculiospp., for example Curculio caryae, Curculio caryatrypes, Curculioobtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus,Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturusspp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestesspp., Diabrotica spp., for example Diabrotica balteata, Diabroticabarberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctataundecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgiferazeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachnaspp., for example Epilachna borealis, Epilachna varivestis, Epitrixspp., for example Epitrix cucumeris, Epitrix fuscula, Epitrixhirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.,Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychusarator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hyperapostica, Hypomeces squamosus, Hypothenemus spp., for exampleHypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens,Lachnosterna consanguinea, Lasioderma serricome, Latheticus oryzae,Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp.,for example Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp.,Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp.,Melanotus spp., for example Melanotus longulus oregonensis, Meligethesaeneus, Melolontha spp., for example Melolontha melolontha, Migdolusspp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagusoryzae, Otiorhynchus spp., for example Otiorhynchus cribricollis,Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchusrugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedoncochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp.,for example Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotretaramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp.,Prostephanus truncatus, Psylliodes spp., for example Psylliodes affinis,Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobiusventralis, Rhizopertha dominica, Sitophilus spp., for example Sitophilusgranarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais,Sphenophorus spp., Stegobium paniceum, Stemechus spp., for exampleStemechus paludatus, Symphyletes spp., Tanymecus spp., for exampleTanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebriomolitor, Tenebrioides mauretanicus, Tribolium spp., for exampleTribolium audax, Tribolium castaneum, Tribolium confusum, Trogodermaspp., Tychius spp., Xylotrechus spp., Zabrus spp., for example Zabrustenebrioides;

from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Fanniaspp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrelliaspp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp.,Liriomyza spp., for example Liriomyza brassicae, Liriomyza huidobrensis,Liriomyza sativae, Lucilia spp., for example Lucilia cuprina, Lutzomyiaspp., Mansonia spp., Musca spp., for example Musca domestica, Muscadomestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp.,Paralauterborniella subcincta, Pegomya spp., for example Pegomya betae,Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp.,Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletisspp., for example Rhagoletis cingulata, Rhagoletis completa, Rhagoletisfausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis,Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., forexample Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., for example Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma piri, Aphis spp., for example Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., for example Aspidiotus nerii, Atanus spp., Aulacorthumsolani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspismelaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicorynebrassicae, Cacopsylla spp., for example Cacopsylla pyricola, Calligyponamarginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae,Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis,Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,for example Coccus hesperidum, Coccus longulus, Coccuspseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp.,Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri,Diaspis spp., Drosicha spp., Dysaphis spp., for example Dysaphisapiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp.,Empoasca spp., for example Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., for exampleEriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana,Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis,Hyalopterus pruni, Icerya spp., for example Icerya purchasi, Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., forexample Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., forexample Lepidosaphes ulmi, Lipaphis erysimi, Macrosiphum spp., forexample Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae,Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiellaspp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., for example Myzus ascalonicus, Myzuscerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae,Nasonovia ribisnigri, Nephotettix spp., for example Nephotettixcincticeps, Nephotettix nigropictus, Nilaparvata lugens, Oncometopiaspp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisiamyricae, Paratrioza spp., for example Paratrioza cockerelli, Parlatoriaspp., Pemphigus spp., for example Pemphigus bursarius, Pemphiguspopulivenae, Peregrinus maidis, Phenacoccus spp., for examplePhenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli,Phylloxera spp., for example Phylloxera devastatrix, Phylloxeranotabilis, Pinnaspis aspidistrae, Planococcus spp., for examplePlanococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis,Pseudaulacaspis pentagona, Pseudococcus spp., for example Pseudococcuscalceolariae, Pseudococcus comstocki, Pseudococcus longispinus,Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psyllaspp., for example Psylla buxi, Psylla mali, Psylla pyri, Pteromalusspp., Pyrilla spp., Quadraspidiotus spp., for example Quadraspidiotusjuglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotusperniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., forexample Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphumpadi, Rhopalosiphum rufiabdominale, Saissetia spp., for exampleSaissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetiaoleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidusarticulatus, Sitobion avenae, Sogata spp., Sogatella furcifera,Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., for example Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., for example Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Anasa tristis,Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylommalivida, Cavelerius spp., Cimex spp., for example Cimex adjunctus, Cimexhemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., for example Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horciasnobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossusoccidentalis, Leptoglossus phyllopus, Lygocoris spp., for exampleLygocoris pabulinus, Lygus spp., for example Lygus elisus, Lygushesperus, Lygus lineolaris, Macropes excavatus, Monalonion atratum,Nezara spp., for example Nezara viridula, Oebalus spp., Piesma quadrata,Piezodorus spp., for example Piezodorus guildinii, Psallus spp.,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., for example Athalia rosae, Atta spp., Diprion spp., for exampleDiprion similis, Hoplocampa spp., for example Hoplocampa cookei,Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomoriumpharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp.,Vespa spp., for example Vespa crabro, Xeris spp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber;

from the order of the Isoptera, for example Coptotermes spp., forexample Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp.,Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermesspp., for example Reticulitermes flavipes, Reticulitermes hesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedialeucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon,Alabama spp., for example Alabama argillacea, Amyelois transitella,Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis,Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrixthurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp.,Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposinaniponensis, Cheimatobia brumata, Chilo spp., for example Chiloplejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., forexample Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphaniaspp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium,Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., for exampleEphestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyaspostvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctisspp., for example Euproctis chrysorrhoea, Euxoa spp., Feltia spp.,Galleria mellonella, Gracillaria spp., Grapholitha spp., for exampleGrapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpaspp., for example Helicoverpa armigera, Helicoverpa zea, Heliothis spp.,for example Heliothis virescens, Hofmannophila pseudospretella,Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoriaflavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., forexample Leucoptera coffeella, Lithocolletis spp., for exampleLithocolletis blancardella, Lithophane antennata, Lobesia spp., forexample Lobesia botrana, Loxagrotis albicosta, Lymantria spp., forexample Lymantria dispar, Lyonetia spp., for example Lyonetia clerkella,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitisleda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogoncloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp.,Ostrinia spp., for example Ostrinia nubilalis, Oulema melanopus, Oulemaoryzae, Panolis flammea, Parnara spp., Pectinophora spp., for examplePectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., forexample Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., for example Phyllonorycter blancardella, Phyllonoryctercrataegella, Pieris spp., for example Pieris rapae, Platynota stultana,Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletiaspp., for example Pseudaletia unipuncta, Pseudoplusia includens,Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., for exampleSchoenobius bipunctifer, Scirpophaga spp., for example Scirpophagainnotata, Scotia segetum, Sesamia spp., for example Sesamia inferens,Sparganothis spp., Spodoptera spp., for example Spodoptera eradiana,Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica,Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Teciasolanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella,Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusiaspp., for example Trichoplusia ni, Tryporyza incertulas, Tuta absoluta,Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., for example Locustamigratoria, Melanoplus spp., for example Melanoplus devastator,Paratlanticus ussuriensis, Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example, Ceratophyllus spp.,Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalidesfelis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens,Frankliniella spp., for example Frankliniella fusca, Frankliniellaoccidentalis, Frankliniella schultzei, Frankliniella tritici,Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp.,Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp.,Taeniothrips cardamomi, Thrips spp., for example Thrips palmi, Thripstabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., forexample Scutigerella immaculata;

pests from the phylum of the Mollusca, for example from the class of theBivalvia, for example Dreissena spp.,

and also from the class of the Gastropoda, for example Arion spp., forexample Arion ater rufus, Biomphalaria spp., Bulinus spp., Derocerasspp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelaniaspp., Pomacea spp., Succinea spp.;

animal and human parasites from the phyla of the Platyhelminthes andNematoda, for example Aelurostrongylus spp., Amidostomum spp.,Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephalaspp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp.,Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp.,Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp.,Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilariaspp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobiusspp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsisspp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronemaspp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepisspp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylusspp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muelleriusspp., Necator spp., Nematodirus spp., Nippostrongylus spp.,Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp.,Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp.,Parafilaria spp., Paragonimus spp., Paramphistomum spp.,Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylusspp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilariaspp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamusspp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp.,Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylusspp., Trichuris spp., Uncinaria spp., Wuchereria spp.;

plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, especially Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorusspp., for example Longidorus africanus, Meloidogyne spp., for exampleMeloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla,Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp.,Paraphelenchus spp., Paratrichodorus spp., for example Paratrichodorusminor, Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

In addition, it is possible to control, from the sub-kingdom of theProtozoa, the order of the Coccidia, for example Eimeria spp.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). If appropriate, they can also be used as intermediates orprecursors for the synthesis of other active ingredients.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I). In somecases, the use forms comprise further pesticides and/or adjuvants whichimprove action, such as penetrants, e.g. vegetable oils, for examplerapeseed oil, sunflower oil, mineral oils, for example paraffin oils,alkyl esters of vegetable fatty acids, for example rapeseed oil methylester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders,for example alkylsiloxanes and/or salts, for example organic orinorganic ammonium or phosphonium salts, for example ammonium sulphateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulphosuccinate or hydroxypropylguar polymers and/or humectants,for example glycerol and/or fertilizers, for example ammonium-,potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemically active ingredients.

These are preferably formulations or use forms which compriseauxiliaries, for example extenders, solvents, spontaneity promoters,carriers, emulsifiers, dispersants, frost protectants, biocides,thickeners and/or further auxiliaries, for example adjuvants. Anadjuvant in this context is a component which improves the biologicalactivity of the formulation without having biological activity itself.Examples of adjuvants are agents which promote retention, the spreadingcharacteristics, adhesion to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) with auxiliaries, for exampleextenders, solvents and/or solid carriers and/or other auxiliaries, forexample surfactants. The formulations are produced either in suitablefacilities or else before or during application.

The auxiliaries used may be such substances suitable for impartingspecial properties, such as certain physical, technical and/orbiological properties, to the formulation of the compounds of theformula (I), or to the use forms prepared from these formulations (forexample ready-to-use pesticides such as spray liquors or seed dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsessentially include: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

In principle, it is possible to use any suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, suchas chlorobenzene, chloroethylene or methylene chloride, aliphatichydrocarbons, such as cyclohexane, paraffins, petroleum fractions,mineral and vegetable oils, alcohols, such as methanol, ethanol,isopropanol, butanol or glycol and their ethers and esters, ketones suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethyl sulphoxide, andalso water.

In principle, it is possible to use all suitable carriers. Usefulcarriers especially include: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and natural or syntheticsilicates, resins, waxes and/or solid fertilizers. It is likewisepossible to use mixtures of such carriers. Useful carriers for granulesinclude: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite, dolomite, and synthetic granules ofinorganic and organic meals, and also granules of organic material suchas sawdust, paper, coconut shells, corn cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable are those extenders or carriers which are gaseous atstandard temperature and under standard pressure, for example aerosolpropellants such as halohydrocarbons, or else butane, propane, nitrogenand carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulphonic acid, salts of phenolsulphonic acid ornaphthalenesulphonic acid, polycondensates of ethylene oxide with fattyalcohols or with fatty acids or with fatty amines, with substitutedphenols (preferably alkylphenols or arylphenols), salts ofsulphosuccinic esters, taurine derivatives (preferably alkyl taurates),phosphoric esters of polyethoxylated alcohols or phenols, fatty acidesters of polyols, and derivatives of the compounds containingsulphates, sulphonates and phosphates, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surfactant is advantageous if one of the compounds of theformula (I) and/or one of the inert carriers is insoluble in water andwhen the application takes place in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom are dyes such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients andtrace nutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

In addition, stabilizers, such as low-temperature stabilizers,preservatives, antioxidants, light stabilizers or other agents whichimprove chemical and/or physical stability, may be present. In addition,foam formers or defoamers may be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders,granules or latices, such as gum arabic, polyvinyl alcohol and polyvinylacetate, or else natural phospholipids such as cephalins and lecithinsand synthetic phospholipids. Further possible auxiliaries are mineraland vegetable oils.

Optionally, yet further auxiliaries may be present in the formulationsand the use forms derived therefrom. Examples of such additives arefragrances, protective colloids, binders, adhesives, thickeners,thixotropic agents, penetrants, retention promoters, stabilizers,sequestrants, complexing agents, humectants, spreaders. In general, thecompounds of the formula (I) can be combined with any solid or liquidadditive commonly used for formulation purposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulphosuccinate, orincrease viscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances whichare typically used to improve the penetration of active agrochemicalingredients into plants. Penetrants are defined in this context by theirability to penetrate from the (generally aqueous) application liquorand/or from the spray coating into the cuticle of the plant and henceincrease the mobility of active ingredients in the cuticle. The methoddescribed in the literature (Baur et al., 1997, Pesticide Science 51,131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I), with particular preferencebetween 0.01% and 95% by weight of the compound of the formula (I), morepreferably between 0.5% and 90% by weight of the compound of the formula(I), based on the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) can also be used in a mixture with oneor more suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active ingredient combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessability of the harvested products.

In addition, the compounds of the formula (I) may be present in amixture with other active ingredients or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used in mixtures with agents to improve plant properties, forexample growth, yield and quality of the harvested material.

In a particular embodiment of the invention, the compounds of theformula (I) are in the form of formulations or the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in various tautomericforms, these forms are also included even if not explicitly mentioned ineach case.

Insecticides/acaricides/nematicides

The active ingredients specified here with their “common names” areknown and are described for example in The Pesticide Manual, 16^(th)ed., British Crop Protection Council 2012.

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos,chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon,dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton,EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,fosthiazate, heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel antagonists, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators/voltage-gated sodium channel blockers, forexample pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin,d-trans allethrin, bifenthrin, bioallethrin, bioallethrins-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin,empenthrin [(EZ)-(1R) isomers], esfenvalerate, etofenprox,fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-transisomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen,tefluthrin, tetramethrin, tetramethrin [(1R) isomers)], tralomethrin andtransfluthrin or DDT or methoxychlor.

(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for exampleneonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor.

(5) Allosteric activators of the nicotinergic acetylcholine receptor(nAChR), for example spinosyns, e.g. spinetoram and spinosad.

(6) Chloride channel activators, for example, avermectins/milbemycins,e.g. abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone imitators, for example, juvenile hormone analoguese.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Active ingredients with unknown or nonspecific mechanisms of action,for example

alkyl halides, e.g. methyl bromide and other alkyl halides; orchloropicrine or sulphuryl fluoride or borax or tartar emetic.

(9) Selective antifeedants, e.g. pymetrozine or flonicamid.

(10) Mite growth inhibitors, e.g. clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect gut membrane, e.g. Bacillusthuringiensis subspecies israelensis, Bacillus sphaericus, Bacillusthuringiensis subspecies aizawai, Bacillus thuringiensis subspecieskurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plantproteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,Cry34/35Ab1.

(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron or organotin compounds, e.g. azocyclotin, cyhexatin andfenbutatin oxide or propargite or tetradifon.

(13) Oxidative phosphorylation decouplers that interrupt the H protongradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinergic acetylcholine receptor antagonists, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Chitin biosynthesis inhibitors, type 0, for example bistrifluron,chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron andtriflumuron.

(16) Chitin biosynthesis inhibitors, type 1, for example buprofezin.

(17) Moulting inhibitors (especially for Diptera, i.e. dipterans), forexample cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists, for example amitraz.

(20) Complex-III electron transport inhibitors, for examplehydramethylnon or acequinocyl or fluacrypyrim.

(21) Complex-I electron transport inhibitors, for example METIacaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-gated sodium channel blockers, for example indoxacarb ormetaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Complex-IV electron transport inhibitors, for example phosphines,e.g. aluminium phosphide, calcium phosphide, phosphine and zincphosphide or cyanide.

(25) Complex-II electron transport inhibitors, for example cyenopyrafenand cyflumetofen.

(28) Ryanodine receptor effectors, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active ingredients, for example afidopyropen, azadirachtin,benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat,cryolite,

dicofol, diflovidazin, fluensulfone, flometoquin, flufenerim,flufenoxystrobin, flufiprole, fluopyram, flupyradifurone, fufenozide,heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding,pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin andiodomethane; and also preparations based on Bacillus firmus (I-1582,BioNeem, Votivo), and also the following compounds:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from WO2005/077934) and1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (knownfrom WO2003/106457),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonate(known from WO2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160),4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known fromWO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide(known from WO2005/085216),4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthamide(known from WO2009/002809), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbony1}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (knownfrom WO2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from CN102057925),3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]phthalamide(known from WO2012/034472),8-chloro-N-[(2-chloro-5-methoxyphenyl)sulphonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide(known from WO2010/129500),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2009/080250),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2012/029672),1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),(5S,8R)-1-[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine(known from WO2010/069266),(2E)-1-[(6-chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide(known from WO2010/060231),4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN101337940),N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO2008/134969).

Fungicides

The active ingredients specified herein by their common name are knownand described, for example, in the “Pesticide Manual”.

(1) Ergosterol biosynthesis inhibitors, for example (1.1) aldimorph,(1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5)cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8)diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, (1.11) dodemorphacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol,(1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18)fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21)flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24)furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalilsulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole,(1.31) myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34)oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole,(1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44)quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47)tebuconazole, (1.48) terbinafin, (1.49) tetraconazole, (1.50)triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole,(1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57)uniconazole-P, (1.58) viniconazole, (1.59) voriconazole, (1.60)1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,(1.62)N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,(1.63)N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideand (1.64)O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate,(1.65) pyrisoxazole.

(2) Respiration inhibitors (respiratory chain inhibitors), for example(2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5)fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8) fluxapyroxad, (2.9)furametpyr, (2.10) furmecyclox, (2.11) isopyrazam mixture of thesyn-epimeric racemate 1RS,4SR,9RS and the anti-empimeric racemate1RS,4SR,9SR, (2.12) isopyrazam (anti-epimeric racemate), (2.13)isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam(anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18)mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad,(2.22) sedaxane, (2.23) thifluzamide, (2.24)1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.25)3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,(2.26)3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.28)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4-amine,(2.29) benzovindiflupyr,(2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideand(2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.32)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.33)1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.34)1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.35)1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.36)1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.37)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.38) 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.39)1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.40)1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.41) benodanil, (2.42)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(2.43) isofetamid

(3) Respiration inhibitors (respiratory chain inhibitors) that act oncomplex III of the respiratory chain, for example (3.1) ametoctradin,(3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid, (3.5)coumethoxystrobin, (3.6) coumoxystrobin, (3.5) dimoxystrobin, (3.8)enestroburin, (3.9) famoxadone, (3.10) fenamidone, (3.11)flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14)metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17)pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20)pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23)(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(3.24)(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,(3.25)(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.27)(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.28)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(3.29)5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(3.30) methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyprop-2-enoate,(3.31)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,(3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide

(4) inhibitors of mitosis and cell division, for example (4.1) benomyl,(4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5)ethaboxam, (4.6) fluopicolid, (4.7) fuberidazole, (4.8) pencycuron,(4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate,(4.12) zoxamide, (4.13)5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidineand (4.14)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

(5) Compounds having multisite activity, for example (5.1) Bordeauxmixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5)copper preparations such as copper hydroxide, (5.6) copper naphthenate,(5.7) copper oxide, (5.8) copper oxychloride, (5.9) copper sulphate,(5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13) dodinefree base, (5.14) ferbam, (5.15) fluorfolpet, (5.16) folpet, (5.17)guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20)iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22)mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zincmetiram, (5.27) copper-oxine, (5.28) propamidine, (5.29) propineb,(5.30) sulphur and sulphur preparations, for example calciumpolysulphide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34)ziram and (5.35) anilazine.

(6) Resistance inducers, for example (6.1) acibenzolar-S-methyl, (6.2)isotianil, (6.3) probenazole, (6.4) tiadinil and (6.5) laminarin.

(7) Amino acid and protein biosynthesis inhibitors, for example (7.1)andoprim, (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin,(7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7)pyrimethanil, (7.8)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolineand (7.9) oxytetracycline and (7.10) streptomycin.

(8) ATP production inhibitors, for example (8.1) fentin acetate, (8.2)fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.

(9) Cell wall synthesis inhibitors, for example (9.1) benthiavalicarb,(9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5)mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A,(9.9) valifenalate and (9.10) polyoxin B.

(10) Lipid and membrane synthesis inhibitors, for example (10.1)biphenyl, (10.2) chlorneb, (10.3) dicloran, (10.4) edifenphos, (10.5)etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8) isoprothiolane,(10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11)prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazeneand (10.15) tolclofos-methyl.

(11) Melanin biosynthesis inhibitors, for example (11.1) carpropamid,(11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilon,(11.6) tricyclazole and (11.7) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

(12) Nucleic acid synthesis inhibitors, for example (12.1) benalaxyl,(12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon,(12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, (12.8)hymexazole, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11)ofurace, (12.12) oxadixyl, (12.13) oxolinic acid and (12.14)octhilinone.

(13) Signal transduction inhibitors, for example (13.1) chlozolinate,(13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5)procymidone, (13.6) quinoxyfen, (13.7) vinclozolin and (13.8)proquinazid.

(14) Decouplers, for example (14.1) binapacryl, (14.2) dinocap, (14.3)ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.

(15) Further compounds, for example (15.1) benthiazole, (15.2)bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5) chinomethionat,(15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyflufenamid,(15.9) cymoxanil, (15.10) cyprosulfamide, (15.11) dazomet, (15.12)debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15)difenzoquat, (15.16) difenzoquat methylsulphate, (15.17) diphenylamine,(15.18) EcoMate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21)fluorimid, (15.22) flusulfamide, (15.23) flutianil, (15.24)fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosetyl-sodium,(15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb,(15.30) methyl isothiocyanate, (15.31) metrafenone, (15.32) mildiomycin,(15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35)nitrothal-isopropyl, (15.36) octhilinone, (15.37) oxamocarb, (15.38)oxyfenthiin, (15.39) pentachlorophenol and its salts, (15.40)phenothrin, (15.41) phosphoric acid and its salts, (15.42)propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrimorph,(15.45)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.46)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.47) pyrrolnitrin, (15.48) tebufloquin, (15.49) tecloftalam, (15.50)tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamid,(15.54)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (15.55)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.56)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.57)1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl1H-imidazole-1-carboxylate, (15.59)2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (15.60)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.62)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.63)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.64)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,(15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(15.67) 2-phenylphenol and salts, (15.68)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(15.71)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,(15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.76)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.77) ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate, (15.78)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.81)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,(15.82)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,(15.83)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,(15.84)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.85)N—{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.86)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(15.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,(15.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.90) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol, (15.93)quinolin-8-ol sulphate (2:1), (15.94) tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.95)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.96)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.97)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.98)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.99)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(15.100)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.101)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.102) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.103)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.104)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.105)3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,(15.106)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.107) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)nicotinamide, (15.108)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.109)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,(15.110)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.111)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.112)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.113)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.114)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.115)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,(15.116)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide,(15.117) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118)but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.120) propyl3,4,5-trihydroxybenzoate, (15.121)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(15.122)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.123)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.124)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.125)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.126)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.127)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.128)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.129)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.130)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.131) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluoropheny)xiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.132)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.133) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.134)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.135)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.136)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.137)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.138)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.139)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.140)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.141)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.142)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.143)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.144) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.145)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.148)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.149) abscisic acid, (15.150)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide,(15.151)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(15.152)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.153)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.154)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.155)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (15.156)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.157)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.158)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.159)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.160)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.161)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.162)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.163)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.164)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.165)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.166)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.167)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-H-pyrazole-4-carboxamide,(15.168)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.169)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.170)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.171)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.172)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(15.173)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.174)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.175)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.176)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamide,(15.177)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(15.178)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.179)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.180)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(15.181)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(15.182)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides include especially bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM 1-1562 or Bacillus firmus,strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421) Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, especially strain ATCC 74040, Coniothyrium minitans,especially strain CON/M/91-8 (Accession No. DSM-9660), Lecanicilliumspp., especially strain HRO LEC 12, Lecanicillium lecanii, (formerlyknown as Verticillium lecanii), especially strain KV01, Metarhiziumanisopliae, especially strain F52 (DSM3884/ATCC 90448), Metschnikowiafructicola, especially strain NRRL Y-30752, Paecilomyces fumosoroseus(now: Isaria fumosorosea), especially strain IFPC 200613, or strainApopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, especiallyP. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, especiallystrain V117b, Trichoderma atroviride, especially strain SC1 (AccessionNumber CBS 122089), Trichoderma harzianum, especially T. harzianum rifaiT39 (Accession Number CNCM 1-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and parts of plants can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya bean, potato, sugarbeet, sugar cane, tomatoes, peas and other vegetable species, cotton,tobacco, oilseed rape, and also fruit plants (with the fruits apples,pears, citrus fruits and grapevines). Crop plants may be plants whichcan be obtained by conventional breeding and optimization methods or bybiotechnological and genetic engineering methods or combinations ofthese methods, including the transgenic plants and including the plantcultivars which are protectable or non-protectable by plant breeders'rights. Parts of plants shall be understood to mean all parts and organsof the plants above and below ground, such as shoot, leaf, flower androot, examples given being leaves, needles, stalks, stems, flowers,fruit bodies, fruits and seeds, and also tubers, roots and rhizomes.Parts of plants also include harvested material and vegetative andgenerative propagation material, for example cuttings, tubers, rhizomes,slips and seeds.

Treatment according to the invention of the plants and plant parts withthe compounds of the formula (I) is carried out directly or by allowingthe compounds to act on their surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering methods, ifappropriate in combination with conventional methods (geneticallymodified organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above. Particularpreference is given in accordance with the invention to treating plantsof the respective commercially customary cultivars or those that are inuse. Plant cultivars are understood to mean plants having new properties(“traits”) and which have been obtained by conventional breeding, bymutagenesis or by recombinant DNA techniques. They may be cultivars,varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher yields, higher quality and/or higher nutritional value of theharvested products, better storage life and/or processibility of theharvested products. Further and particularly emphasized examples of suchproperties are increased resistance of the plants against animal andmicrobial pests, such as insects, arachnids, nematodes, mites, slugs andsnails owing, for example, to toxins formed in the plants, in particularthose produced in the plants by the genetic material from Bacillusthuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c),CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and alsocombinations thereof), and also increased resistance of the plantsagainst phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certainherbicidally active ingredients, for example imidazolinones,sulphonylureas, glyphosates or phosphinothricin (for example the “PAT”gene). The genes which impart the desired properties (“traits”) inquestion may also be present in combinations with one another in thetransgenic plants. Examples of transgenic plants include the importantcrop plants, such as cereals (wheat, rice, triticale, barley, rye,oats), maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes,peas and other types of vegetable, cotton, tobacco, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapes), particular emphasis being given to maize, soya beans, wheat,rice, potatoes, cotton, sugar cane, tobacco and oilseed rape. Properties(“traits”) which are particularly emphasized are the increasedresistance of the plants to insects, arachnids, nematodes and slugs andsnails.

Crop Protection—Types of Treatment

The treatment of the plants and plant parts with the compounds of theformula (I) is carried out directly or by action on their surroundings,habitat or storage space using customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading-on, injecting,watering (drenching), drip irrigating and, in the case of propagationmaterial, in particular in the case of seed, furthermore as a powder fordry seed treatment, a solution for liquid seed treatment, awater-soluble powder for slurry treatment, by incrusting, by coatingwith one or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application, i.e.compounds of the formula (I) are applied to the foliage, where treatmentfrequency and the application rate should be adjusted according to thelevel of infestation with the pest in question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I) areintroduced in solid form (e.g. in the form of granules) into the locusof the plants. In the case of paddy rice crops, this can also beaccomplished by metering the compound of the formula (I) in a solidapplication form (for example as granules) into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements.Nevertheless, the treatment of seed gives rise to a series of problemswhich cannot always be solved in a satisfactory manner. Thus, it isdesirable to develop methods for protecting the seed and the germinatingplant which dispense with, or at least reduce considerably, theadditional application of pesticides during storage, after sowing orafter emergence of the plants. It is additionally desirable to optimizethe amount of active ingredient used so as to provide optimum protectionfor the seed and the germinating plant from attack by animal pests, butwithout damage to the plant itself by the active ingredient used. Inparticular, methods for the treatment of seed should also take accountof the intrinsic insecticidal or nematicidal properties ofpest-resistant or -tolerant transgenic plants in order to achieveoptimal protection of the seed and the germinating plant with a minimumexpenditure of pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants, from attack by pests,by treating the seed with one of the compounds of the formula (I). Theinventive method for protecting seed and germinating plants againstattack by pests further comprises a method in which the seed is treatedsimultaneously in one operation or sequentially with a compound of theformula (I) and a mixing component. It also further comprises a methodwhere the seed is treated at different times with a compound of theformula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) for protection from animal pests. Theinvention also relates to seed which has been treated simultaneouslywith a compound of the formula (I) and a mixing component. The inventionfurther relates to seed which has been treated at different times with acompound of the formula (I) and a mixing component. In the case of seedwhich has been treated at different times with a compound of the formula(I) and a mixing component, the individual substances may be present onthe seed in different layers. In this case, the layers comprising acompound of the formula (I) and a mixing component may optionally beseparated by an intermediate layer. The invention also relates to seedin which a compound of the formula (I) and a mixing component have beenapplied as part of a coating or as a further layer or further layers inaddition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages that occurs when one of the compounds of theformula (I) acts systemically is that the treatment of the seed protectsnot just the seed itself but also the plants resulting therefrom afteremergence against animal pests. In this way, the immediate treatment ofthe crop at the time of sowing or shortly thereafter can be dispensedwith.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

In addition, compounds of the formula (I) can be used in combinationwith signalling technology compositions, which results in bettercolonization by symbionts, for example rhizobia, mycorrhizae and/orendophytic bacteria or fungi, and/or leads to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in greenhouses, inforests or in horticulture. More particularly, this includes seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugarbeets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya, cotton,canola, oilseed rape and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for the treatment of transgenic seed containing atleast one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which, for example, has been pre-swollen in waterup to a particular stage (pigeon breast stage), which leads to bettergermination and to more homogeneous emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activeingredients which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed inthe form of a suitable formulation. Suitable formulations and processesfor seed treatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customary seeddressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are produced in a known manner, by mixing thecompounds of the formula (I) with customary additives, for examplecustomary extenders and solvents or diluents, dyes, wetters,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, stickers, gibberellins and also water.

Useful dyes which may be present in the seed dressing formulationsusable in accordance with the invention are all dyes which are customaryfor such purposes. It is possible to use either pigments, which aresparingly soluble in water, or dyes, which are soluble in water.Examples include the dyes known by the names Rhodamine B, C.I. PigmentRed 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical ingredients. Preference is given to using alkylnaphthalenesulphonates, such as diisopropyl or diisobutylnaphthalenesulphonates.

Suitable dispersants and/or emulsifiers which may be present in the seeddressing formulations usable in accordance with the invention are allnonionic, anionic and cationic dispersants customary for the formulationof active agrochemical compounds. Preference is given to using nonionicor anionic dispersants or mixtures of nonionic or anionic dispersants.Suitable nonionic dispersants include in particular ethyleneoxide/propylene oxide block polymers, alkylphenol polyglycol ethers andtristryrylphenol polyglycol ethers, and the phosphated or sulphatedderivatives thereof. Suitable anionic dispersants are especiallylignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehydecondensates.

Antifoams which may be present in the seed dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for formulation of active agrochemical ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed dressing formulationsusable in accordance with the invention are all customary binders usablein seed dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz-und Schädlingsbekäimpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, soya beans and beets, or else awide variety of different vegetable seed. The seed dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For treatment of seed with the seed dressing formulations usable inaccordance with the invention, or the use forms prepared therefrom, allmixing units usable customarily for the seed dressing are useful.Specifically, the procedure in seed dressing is to place the seed into amixer in batchwise or continuous operation, to add the particulardesired amount of seed dressing formulations, either as such or afterprior dilution with water, and to mix until the formulation isdistributed homogeneously on the seed. If appropriate, this is followedby a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasites”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects and acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable homeotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer,and particularly cattle and pigs; poultry such as turkeys, ducks, geese,and particularly chickens; fish and crustaceans, for example inaquaculture, and also insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds, reptiles, amphibians and aquarium fish.

In a preferred embodiment, the compounds of the formula (I) areadministered to mammals.

In another preferred embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds and particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalkeeping is enabled and better animal well-being is achievable.

In relation to the animal health field, the term “control” or“controlling” means that the compounds of the formula (I) are effectivein reducing the incidence of the particular parasite in an animalinfected with such parasites to an innocuous degree. More specifically,“controlling” in the present context means that the compound of theformula (I) can kill the respective parasite, inhibit its growth, orinhibit its proliferation.

Arthropods Include:

from the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; fromthe order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.; from the order of the Diptera and thesuborders Nematocerina and Brachycerina, for example Aedes spp.,Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomusspp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp.,Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp.,Tipula spp.; from the order of the Siphonapterida, for example Pulexspp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllusspp.;

from the order of the Heteropterida, for example Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.; and also nuisance and hygienepests from the order of the Blattarida.

Arthropods Further Include:

from the subclass of the Acari (Acarina) and the order of theMetastigmata, for example from the family of Argasidae like Argas spp.,Ornithodorus spp., Otobius spp., from the family of Ixodidae like Ixodesspp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the originalgenus of multi-host ticks); from the order of Mesostigmata likeDermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp.,Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; fromthe order of the Actinedida (Prostigmata), for example Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.;and from the order of the Acaridida (Astigmata), for example Acarusspp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichusspp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

Parasitic Protozoa Include:

Mastigophora (Flagellata), for example Trypanosomatidae, for example,Trypanosoma b. brucei, T. b. gambiense, T. b. rhodesiense, T.congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T.simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, forexample Trichomonadidae, for example, Giardia lamblia, G. canis;

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example,Entamoeba histolytica, Hartmanellidae, for example, Acanthamoeba sp.,Harmanella sp.;

Apicomplexa (Sporozoa) such as Eimeridae, for example, Eimeriaacervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E.arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E.chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E.debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E.flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina,E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media,E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E.ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E.phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E.stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuemii,Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I.rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec.,in particular C. parvum; such as Toxoplasmadidae, for example,Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitiabesnoitii; such as

Sarcocystidae, for example, Sarcocystis bovicanis, S. bovihominis, S.ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such asLeucozoidae, for example, Leucozytozoon simondi, such as Plasmodiidae,for example, Plasmodium berghei, P. falciparum, P. malariae, P. ovale,P. vivax, P. spec., such as Piroplasmea, for example, Babesia argentina,B. bovis, B. canis, B. spec., Theileria parva, Theileria spec., such asAdeleina, for example, Hepatozoon canis, H. spec.

Pathogenic endoparasites, which are helminths, include Platyhelmintha(e.g. Monogenea, cestodes and trematodes), roundworms, Acanthocephala,and Pentastoma. These include:

Monogenea: for example: Gyrodactylus spp., Dactylogyrus spp., Polystomaspp.

Cestodes: from the order of the Pseudophyllidea, for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diphlogonoporus spp.;

from the order of the Cyclophyllida, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.;

Trematodes: from the class of the Digenea, for example: Diplostomumspp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciolaspp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp.,Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoronspp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp.,Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimusspp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimusspp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchisspp., Metorchis spp., Heterophyes spp., Metagonimus spp.; nematodes:Trichinellida, for example: Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.;

from the order of the Tylenchida, for example: Micronema spp.,Strongyloides spp.;

from the order of the Rhabditida, for example: Strongylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muelleriusspp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp.,Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.,Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerusspp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp.,Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagiaspp., Teladorsagia spp., Marshallagia spp., Cooperia spp.,Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.;

from the order of the Spirurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;

Acanthocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of thePolymorphida, for example: Filicollis spp.; from the order of theMoniliformida, for example: Moniliformis spp.;

from the order of the Echinorhynchida, for example, Acanthocephalusspp., Echinorhynchus spp., Leptorhynchoides spp.;

Pentastoma: from the order of the Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal keeping, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic ortherapeutic.

Thus, one embodiment of the present invention refers to the use of acompound of the formula (I) as medicament.

A further aspect refers to the use of a compound of the formula (I) asan antiendoparasitic agent, in particular as a helminthicidal agent orantiprotozoic agent. Compounds of the formula (I) are suitable for useas an antiendoparasitic agent, especially as a helminthicidal agent orantiprotozoic agent, for example in animal husbandry, in animalbreeding, in buildings for livestock and in the hygiene sector.

A further aspect in turn relates to the use of a compound of the formula(I) as an antiectoparasitic agent, especially an arthropodicide such asan insecticide or an acaricide. A further aspect relates to the use of acompound of the formula (I) as an antiectoparasitic agent, especially anarthropodicide such as an insecticide or an acaricide, for example inanimal husbandry, in animal breeding, in buildings for livestock or inthe hygiene sector.

Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample, viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) to a host or after injection (for example malaria parasites bymosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

-   1) Mosquitoes    -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of worms;    -   Aedes: yellow fever, dengue fever, filariasis, other viral        diseases;    -   Simuliidae: transmission of worms, in particular Onchocerca        volvulus;-   2) Lice: skin infections, epidemic typhus;-   3) Fleas: plague, endemic typhus;-   4) Flies: sleeping sickness (trypanosomiasis); cholera, other    bacterial diseases;-   5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia,    Saint Louis encephalitis, tick-borne encephalitis (TBE),    Crimean-Congo haemorrhagic fever, borreliosis;-   6) Ticks: borellioses such as Borrelia duttoni, tick-borne    encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia canis    canis).

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, lice, fleas, flies, mites and ticks, whichcan transmit pathogens to animals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, inforestry, in gardens and in leisure facilities, and also in theprotection of materials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) are present asa ready-to-use pesticide, i.e. they can be applied to the material inquestion without further modifications. Suitable further insecticides orfungicides are in particular those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active ingredients, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic sector, in the hygiene sector and in the protectionof stored products, particularly for control of insects, arachnids andmites encountered in enclosed spaces, for example dwellings, factoryhalls, offices, vehicle cabins. For controlling animal pests, thecompounds of the formula (I) are used alone or in combination with otheractive ingredients and/or auxiliaries. They are preferably used indomestic insecticide products. The compounds of the formula (I) areeffective against sensitive and resistant species, and against alldevelopmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

PREPARATION EXAMPLES Preparation Example 13-Methyl-2-[3-(methylsulphonyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(I-36)

41 mg (0.10 mmol) of3-methyl-2-[3-(methylsulphanyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridineare dissolved in 4 ml of dichloromethane, 86.5 mg (0.36 mmol) ofmeta-chloroperbenzoic acid are added at 0° C. and then the mixture isstirred at room temperature for 20 h. The mixture is admixed with sodiumbisulphite solution, stirred for 10 min, diluted with 30 ml of water andadjusted to pH 9-10 with 45% sodium hydroxide solution. The mixture isextracted three times with dichloromethane and then the combined organicphases are freed of the solvent under reduced pressure.

(log P (neutral): 2.64; MH⁺: 425; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 3.70(s, 3H), 3.93 (s, 3H), 8.35 (s, 1H), 8.83 (s, 1H), 9.32 (s, 1H), 9.58(s, 1H).

Preparation of3-methyl-2-[3-(methylsulphinyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifluoro-methyl)-3H-imidazo[4,5-c]pyridine(I-26)

41 mg (0.10 mmol) of3-methyl-2-[3-(methylsulphanyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridineare dissolved in 4 ml of dichloromethane, and 1.92 mg (0.04 mmol) offormic acid and 28.44 mg of a 35% hydrogen peroxide solution are addedat room temperature. The mixture is stirred at room temperature for 5 h,sodium bisulphite solution is added and the mixture is stirred for afurther 3 h. Subsequently, the mixture is stirred with 10% sodiumhydrogencarbonate solution, the organic phase is removed, the aqueousphase is extracted twice with dichloromethane, and the organic phasesare combined and then freed of the solvent under reduced pressure.

(log P (neutral): 2.76; MH⁺: 409; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 3.15(s, 3H), 4.35 (s, 3H), 8.37 (s, 1H), 8.85 (s, 1H), 9.37 (s, 1H), 9.39(s, 1H).

Preparation of3-methyl-2-[3-(methylsulphanyl)-5-(trifluoromethyl)pyridin-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(I-3)

150 mg (0.39 mmol) of2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridineand 83 mg (1.18 mmol) of sodium methanethiolate are stirred in DMF atroom temperature for 6 h. The mixture is admixed with water andextracted three times with ethyl acetate. The combined organic phasesare washed with a sodium chloride solution, removed, dried over sodiumsulphate and freed of the solvent under reduced pressure.

(log P (neutral): 3.16; MH⁺: 393; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 2.58(s, 3H), 4.06 (s, 3H), 8.27 (s, 1H), 8.32 (s, 1H), 8.95 (s, 1H), 9.29(s, 1H).

Preparation of2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(IX-01)

950 mg (4.97 mmol) of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine(II-01), 1.12 g (4.97 mmol) of3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid and 953 mg (4.97mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(EDCI) are stirred in 10 ml of pyridine at 115° C. for 7 h. The reactionmixture is freed of solvent under reduced pressure, then water is addedand the mixture is extracted three times with ethyl acetate. Thecombined organic phases are dried over sodium sulphate, concentratedagain and purified by column chromatography purification by means ofpreparative HPLC with a water/acetonitrile gradient as eluent.

(log P (neutral): 2.96; MH⁺: 381; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 4.00(s, 3H), 8.35 (s, 1H), 8.86 (s, 1H), 9.22 (s, 1H), 9.30 (s, 1H).

Preparation of3-chloro-N-[5-(methylamino)-2-(trifluoromethyl)pyridin-4-yl]-5-(trifluoromethyl)pyridine-2-carboxamide(VIII-01)

By the above method for preparation of2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(IX-01) from N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (II-01)and 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, it islikewise possible to prepare the compound3-chloro-N-[5-(methylamino)-2-(trifluoromethyl)pyridin-4-yl]-5-(trifluoromethyl)pyridine-2-carboxamide(VIII-01) as an intermediate for the compound (IX-01).

(log P (neutral): 3.09; MH⁺: 399; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 2.87(d, 3H), 5.97 (q, 1H), 8.10 (s, 1H), 8.18 (s, 1H), 8.73 (s, 1H), 9.09(s, 1H), 10.40 (br. S, 1H).

Preparation of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (II-01)

A solution of 0.93 g (3.0 mmol) of benzyl[4-amino-6-(trifluoromethyl)pyridin-3-yl]carbamate in 85 ml oftetrahydrofuran is cooled to 0° C. and admixed with 0.65 g (17 mmol) oflithium aluminium hydride. The mixture is stirred under argon at 0° C.for 15 min and then at room temperature for 4 h. The excess of lithiumaluminium hydride is destroyed by the addition of ethyl acetate, themixture is filtered and the filtrate is extracted twice with 50 ml eachtime of 2 N hydrochloric acid. The combined hydrochloric acid extractsare adjusted to pH=8 with sodium carbonate while cooling. Subsequently,the mixture is extracted twice with 100 ml each time of ethyl acetate,the organic phases are combined and dried with sodium sulphate, and thesolvent is distilled off under reduced pressure. The product is purifiedfurther by recrystallization from a mixture of hexane/isopropanol.

(MH⁺: 192; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 2.81 (d, 3H), 5.22 (q, 1H),5.82 (br. s, 2H), 6.84 (s, 1H), 7.57 (s, 1H).

Preparation of benzyl [4-amino-6-(trifluoromethyl)pyridin-3-yl]carbamate

0.91 g of 6-(trifluoromethyl)pyridine-3,4-diamine is dissolved in amixture of 20 ml of tetrahydrofuran and 2 ml of pyridine. A solution of1.07 g (6.3 mmol) of benzyl chlorocarbonate (benzyl chloroformate) in 2ml of tetrahydrofuran is added dropwise while stirring. Subsequently,the reaction mixture is stirred overnight, diluted with 100 ml of waterand extracted twice with 100 ml each time of ethyl acetate. The combinedorganic phases are washed with 50 ml of water, dried over sodiumsulphate and concentrated.

By washing the residue with 50 ml of chloroform, the product is obtainedin the form of a white solid.

(¹H NMR (500 MHz, D₆-DMSO) δ ppm: 5.15 (s, 2H), 6.40 (br. s 2H), 7.05(s, 1H), 7.30-7.45 (m, 5H), 8.35 (s, 1H), 9.00 (br. s, 1H).

Preparation Example 22-[2-(Ethylsulphanyl)phenyl]-6-(trifluoromethyl)[1,3]oxazolo[5,4-c]pyridine(I-35)

400 mg (1.16 mmol) of2-(ethylsulphanyl)-N-[5-hydroxy-2-(trifluoromethyl)pyridin-4-yl]benzamideand 398 mg (1.51 mmol) of triphenylphosphine are dissolved in 12 ml ofTHF, and 661 mg (1.51 mmol) of 40% diethyl azodicarboxylate (DEAD) intoluene are added dropwise at RT. The mixture is stirred at roomtemperature for 3 h. Subsequently, the solvent is distilled off underreduced pressure and the residue is purified by column chromatographypurification with a water/acetonitrile gradient as eluent.

(log P (neutral): 4.07; MH⁺: 325; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 1.32(t, 3H), 3.10 (q, 2H), 7.42 (t, 1H), 7.60-7.69 (m, 2H), 8.21 (d, 1H),8.54 (s, 1H), 9.33 (s, 1H).

Preparation of2-(ethylsulphanyl)-N-[5-hydroxy-2-(trifluoromethyl)pyridin-4-yl]benzamide(VIII-02)

206 mg (1.12 mmol) of 2-(ethylsulphanyl)benzoic acid and 201 mg (1.12mmol) of 4-amino-6-(trifluoromethyl)pyridin-3-ol are dissolved in 5 mlof pyridine, 325 mg (1.69 mmol) of1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) areadded and the mixture is stirred at 50° C. for 2 h and at 80° C. for 3h. The solvent is distilled off under reduced pressure, and the residueis taken up in water and extracted with ethyl acetate. The organic phaseis washed with a sodium chloride solution, removed, dried over sodiumsulphate and concentrated. The residue is purified by columnchromatography purification by means of preparative HPLC with awater/acetonitrile gradient as eluent.

(log P (neutral): 1.59; MH⁺: 343; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 1.21(t, 3H), 2.98 (q, 2H), 7.29-7.34 (m, 1H), 7.48-7.53 (m, 2H), 7.61 (d,1H), 8.29 (s, 1H), 8.55 (s, 1H), 9.99 (s, 1H), 11.31 (br. S, 1H).

Preparation of 4-amino-6-(trifluoromethyl)pyridin-3-ol (II-02)

12.3 g (42.1 mmol) of tert-butyl[5-methoxy-2-(trifluoromethyl)pyridin-4-yl]carbamate are dissolved in300 ml of dichloromethane and cooled to −78° C., and 42.2 g (168 mmol)of boron tribromide in 150 ml of dichloromethane are added dropwise atthis temperature. The mixture is allowed to come to room temperatureovernight, then 400 ml of sodium hydrogencarbonate solution are addedand the mixture is extracted three times with 100 ml each time ofdichloromethane. The solvent is distilled off and the residue ispurified by chromatography on silica gel.

(¹H NMR (90 MHz, D₆-DMSO) δ ppm: 7.00 (s, 1H), 7.9 (s, 1H).

Preparation of tert-butyl[5-methoxy-2-(trifluoromethyl)pyridin-4-yl]carbamate

To a solution of 9.80 g (44.3 mmol) of5-methoxy-2-(trifluoromethyl)isonicotinic acid in 980 ml of tert-butanolare added, at room temperature, 65 g of 4 A molecular sieve, 14.6 g(53.1 mmol) of diphenylphosphoryl azide (DPPA) and 5.37 g (53.1 mmol) oftriethylamine. The reaction mixture is stirred at 81° C. for 23 h andthen the 4 A molecular sieve is filtered off. After the tert-butanol hasbeen distilled off under reduced pressure, the residue is admixed with500 ml of ethyl acetate, washed with 250 ml of 2 N hydrochloric acid,250 ml of saturated aqueous sodium hydrogencarbonate solution, 250 ml ofwater and 250 ml of sodium chloride solution, and dried over sodiumsulphate. The solvent is removed under reduced pressure and the residueis washed three times with 15 ml each time of ethyl acetate and driedunder reduced pressure. The ethyl acetate phase is purified bychromatography on silica gel (hexane/EtOAc 4:1=>2:1).

(¹H NMR (90 MHz, CDCl₃) δ ppm: 1.5 (s, 9H), 4.0 (s, 3H), 8.2 (s, 1H),8.5 (s, 1H).

Preparation of2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)-phenyl]imidazo[4,5-c]pyridine(I-64)

A solution of 62 mg (0.58 mmol) of sodium carbonate in 2 ml of a 4:1mixture of 1,2-dimethoxyethane and water is degassed in an ultrasoundbath, and 73 mg (0.19 mmol) of6-chloro-2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methylimidazo[4,5-c]pyridineand 67 mg (0.35 mmol) of [4-(trifluoromethyl)phenyl]boronic acid areadded. The vessel is flooded with argon and then 23 mg (20 μmol) oftetrakis(triphenylphosphine)palladium are added. The mixture is heatedin a CEM Discover microwave to 140° C. for 2 h 10 min, then admixed witha further 68 mg (59 μmol) of tetrakis(triphenylphosphine)palladium andheated to 140° C. for a further 4 h. The reaction mixture is filteredthrough a Celite bed which has been rinsed with ethyl acetate. After thesolvent has been removed under reduced pressure, the residue isseparated chromatographically by MPLC on silica gel (gradient: ethylacetate/cyclohexane). This is followed by another chromatographicseparation by means of preparative HPLC (gradient: H₂O/acetonitrile). Inthis way, 14 mg (99% purity, 15% yield) of2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)phenyl]imidazo[4,5-c]pyridineare obtained.

(log P (neutral): 3.95; MH⁺: 483; ¹H NMR (400 MHz, D₆-DMSO) δ ppm: 9.275(2.6); 9.271 (2.5); 8.943 (4.3); 8.584 (2.6); 8.580 (2.6); 8.318 (0.5);7.701 (3.0); 7.680 (3.9); 7.548 (3.8); 7.527 (3.0); 7.410 (4.6); 3.890(16.0); 3.329 (75.4); 3.140 (1.3); 3.122 (4.2); 3.104 (4.3); 3.086(1.4); 2.676 (0.9); 2.671 (1.2); 2.667 (0.9); 2.507 (140.3); 2.502(179.9); 2.498 (134.5); 2.334 (0.9); 2.329 (1.2); 2.325 (0.9); 1.281(4.6); 1.263 (9.7); 1.245 (4.5); 0.146 (0.4); 0.008 (3.6); 0.000 (84.0);-0.150 (0.4).

Preparation of2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)-imidazol-1-yl]imidazo[4,5-c]pyridine(I-74)

Under argon, 99 mg (0.27 mmol) of6-chloro-2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methylimidazo[4,5-c]pyridine,23 μl (0.15 mmol) of trans-N,N′-dimethylcyclohexane-1,2-diamine, 6.8 mg(36 μmol) of copper(I) iodide, 30 mg (0.22 mmol) of4-(trifluoromethyl)-1H-imidazole and 64 mg (0.46 mmol) of potassiumcarbonate are added to 1 ml of degassed toluene. The vessel is closedand the reaction mixture is heated in a CEM Discover microwave reactorto 110° C. for 4 h. After cooling to room temperature, ethyl acetate isadded and the mixture is filtered through a Celite bed, which issubsequently rinsed with ethyl acetate. The solvent is removed underreduced pressure and the residue is separated chromatographically byMPLC on silica gel (gradient: ethyl acetate/cyclohexane). In this way,22 mg (100% purity, 18% yield) of2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)imidazol-1-yl]imidazo[4,5-c]pyridineare obtained.

(log P (neutral): 3.36; MH⁺: 473; ¹H NMR (600 MHz, CD₃CN) δ ppm: 8.905(3.0); 8.903 (3.0); 8.852 (1.6); 8.850 (1.6); 8.500 (1.9); 8.313 (1.5);8.311 (2.1); 8.309 (1.4); 8.183 (1.7); 8.181 (1.7); 7.962 (3.4); 7.961(3.4); 4.001 (16.0); 3.940 (0.4); 3.124 (1.1); 3.111 (3.4); 3.099 (3.5);3.087 (1.2); 2.639 (0.7); 2.184 (55.7); 2.109 (1.2); 2.005 (2.2); 1.998(195.7); 1.989 (2.7); 1.985 (1.8); 1.981 (10.0); 1.977 (18.2); 1.973(26.5); 1.969 (18.0); 1.965 (9.0); 1.882 (1.2); 1.419 (0.4); 1.404(0.7); 1.373 (0.6); 1.330 (4.1); 1.318 (9.0); 1.309 (1.6); 1.305 (5.2);1.301 (3.4); 0.914 (0.6).

In analogy to the examples and according to the above-describedpreparation processes, the following compounds of the formula (I) can beobtained:

where A³ is oxygen and the other substituents are each as defined in thefollowing table:

Ex. R¹ N A⁴ A⁵ R³ A² A¹ R^(2a) R^(2b) I-1 CH₃ 0 N CH CF₃ O CH Cl H I-2C₂H₅ 0 CH CH CF₃ N-methyl N CF₃ H I-3 CH₃ 0 CH CH CF₃ N-methyl N CF₃ HI-4 CH₃ 0 CH CH CF₃ N-methyl CH F H I-5 CH₃ 0 CH CH CF₃ N-methyl CH CF₃H I-6 CH₃ 0 N CH CF₃ N-methyl CH Cl H I-7 —(CH₂)₂—SO₂—C₂H₅ 2 CH CH CF₃N-methyl N CF₃ H I-8 i-C₃H₇ 1 CH CH CF₃ N-methyl N CF₃ H I-9 C₂H₅ 0 N CHCF₃ O CH H H I-10 CH₃ 1 CH CH CF₃ N-methyl CH Cl H I-11 CH₃ 2 CH CH CF₃N-methyl CH Cl H I-12 CH₃ 1 CH CH CF₃ N-methyl CH F H I-13 C₂H₅ 1 CH CHCF₃ N-methyl CH H 5-Cl* I-14 CH₃ 2 CH CH CF₃ N-methyl CH 3 H I-15 C₂H₅ 2CH CH CF₃ N-methyl N H H I-16 i-C₃H₇ 2 CH CH CF₃ N-methyl N CF₃ H I-17C₂H₅ 0 CH CH CF₃ N-methyl CH H H I-18 C₂H₅ 2 CH CH CF₃ N-methyl CH H HI-19 C₂H₅ 0 CH CH CF₃ N-methyl CH H 5-Cl* I-20 CH₃ 2 CH CH CF₃ N-methylCH F H I-21 C₂H₅ 2 CH CH CF₃ N-methyl N CF₃ H I-22 C₂H₅ 1 CH CH CF₃N-methyl CH H H I-23 —(CH₂)₂—S—C₂H₅ 0 CH CH CF₃ N-methyl N CF₃ H I-24C₂H₅ 0 CH CH CF₃ N-methyl N H H I-25 CH₃ 0 CH CH CF₃ N-methyl CH Cl HI-26 CH₃ 1 CH CH CF₃ N-methyl N CF₃ H I-27 oxetan-3-yl 2 CH CH CF₃N-methyl CH H H I-28 C₂H₅ 0 N CH CF₃ N-methyl N CF₃ H I-29 CF₃ 0 CH CHCF₃ N-methyl N H H I-30 CH₃ 1 CH CH CF₃ N-methyl CH CF₃ H I-31 n-C₃H₇ 0CH CH CF₃ N-methyl N CF₃ H I-32 n-C₃H₇ 2 CH CH CF₃ N-methyl N CF₃ H I-33C₂H₅ 1 CH CH CF₃ N-methyl N H H I-34 CH₃ 0 CH CH CF₃ O CH Cl H I-35 C₂H₅0 CH CH CF₃ O CH H H I-36 CH₃ 2 CH CH CF₃ N-methyl N CF₃ H I-37 C₂H₅ 1CH CH CF₃ N-methyl N CF₃ H I-38 C₂H₅ 2 CH CH CF₃ N-methyl CH H 5-Cl*I-39 n-C₃H₇ 1 CH CH CF₃ N-methyl N CF₃ H I-40 oxetan-3-yl 0 CH CH CF₃ OCH H H I-41 i-C₃H₇ 0 CH CH CF₃ N-methyl N CF₃ H I-42 C₂H₅ 0 CH CH CF₃N-methyl CH Cl H I-43 C₂H₅ 2 CH CH CF₃ N-methyl CH Cl H I-44 C₂H₅ 1 CHCH CF₃ N-methyl CH Cl H I-45 C₂H₅ 2 CH CH CF₃ N-methyl N H 5-OMe* I-46C₂H₅ 0 CH CH C₂F₅ N-methyl N H H I-47 C₂H₅ 0 CH CH C₂F₅ N-methyl N CF₃ HI-48 C₂H₅ 2 CH CH CF₃ N-methyl N H 3-CF₃* I-49 C₂H₅ 2 CH CH CF₃ N-methylN H 5-NHCOMe* I-50 C₂H₅ 0 CH CH CF₃ N-methyl N H 5-NHCOMe* I-51 C₂H₅ 1CH CH CF₃ N-methyl N H 3-CF₃* I-52 C₂H₅ 2 CH CH Cl N-methyl N CF₃ H I-53C₂H₅ 0 CH CH CF₃ N-methyl N H 5-OMe* I-54 CH₂—CH₂F 2 CH CH CF₃ N-methylN CF₃ H I-55 C₂H₅ 0 CH CH Cl N-methyl N CF₃ H I-56 C₂H₅ 2 CH CH CF₃N-methyl N CONH₂ H I-57 CH₂—CH₂F 2 CH CH CF₃ N-methyl N CF₃ H I-58CH₂—CH₂OH 2 CH CH CF₃ N-methyl N CF₃ H I-59 CH₂—CH₂OH 0 CH CH CF₃N-methyl N CF₃ H I-60 C₂H₅ 0 CH CH CF₃ N-methyl N CONH₂ H I-61 C₂H₅ 1 CHCH C₂F₅ N-methyl N H H I-62 C₂H₅ 2 CH CH CF₃ N-methyl CH H 3-Cl* I-63C₂H₅ 1 CH CH C₂F₅ N-methyl N CF₃ H I-64 C₂H₅ 0 CH CH 4-CF₃(C₆H₄)N-methyl N CF₃ H I-65 C₂H₅ 0 CH CH 4-(CF₃)pyrazol-1-yl N-methyl N CF₃ HI-66 n-C₃H₇ 0 CH CH CF₃ N-methyl N H 5-OMe* I-67 CH₃ 0 CH CH CF₃N-methyl N H 5-OMe* I-68 C₂H₅ 2 CH CH C₂F₅ N-methyl N H H I-69 C₂H₅ 0 CHCH 3-(CF₃)pyrazol-1-yl N-methyl N CF₃ H I-70 C₂H₅ 0 CH CH CF₃ N-methyl NH 3-CF₃* I-71 n-C₃H₇ 2 CH CH CF₃ N-methyl N H 5-OMe* I-72 C₂H₅ 2 CH CHCF₃ N-methyl N CN H I-73 CH₃ 2 CH CH CF₃ N-methyl N H 5-OMe* I-74 C₂H₅ 0CH CH 4-(CF₃)imidazol-1-yl N-methyl N CF₃ H I-75 C₂H₅ 2 CH CH4-(CF₃)imidazol-1-yl N-methyl N CF₃ H I-76 C₂H₅ 2 CH CH4-(CF₃)pyrazol-1-yl N-methyl N CF₃ H I-77 C₂H₅ 2 CH CH3-(CF₃)pyrazol-1-yl N-methyl N CF₃ H *In these examples, R^(2b) isjoined in the 3 or 5 position:

The log P values are measured according to EEC Directive 79/831 AnnexV.A8 by HPLC (high-performance liquid chromatography) on areversed-phase column (C 18). Temperature: 55° C.

The LC-MS determination in the acidic range is effected at pH 2.7 using0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) aseluents, linear gradient from 10% acetonitrile to 95% acetonitrile.Called log P (HCOOH) in the table.

LC-MS determination in the neutral range is effected at pH 7.8 with0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrileas eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.Called log P (neutral) in the table.

Calibration is effected with unbranched alkan-2-ones (having 3 to 16carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR data for selected examples are listed either in conventionalform (6 values, multiplet splitting, number of hydrogen atoms) or as NMRpeak lists.

The solvent in which the NMR spectrum was recorded is reported in eachcase.

NMR Peak List Method

The ¹H NMR data of selected examples are reported in the form of ¹H NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The δ value—signalintensity number pairs for different signal peaks are listed withseparation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of ¹H NMR spectra we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra measured in DMSO. Therefore, thetetramethylsilane peak may, but need not, occur in NMR peak lists.

The lists of the ¹H NMR peaks are similar to the conventional ¹H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional ¹H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds, whichlikewise form part of the subject-matter of the invention, and/or peaksof impurities.

In the reporting of compound signals in the delta range of solventsand/or water, our lists of ¹H NMR peaks show the usual solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in this case to identifyreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional ¹H NMRinterpretation.

Further details of ¹H NMR peak lists can be found in Research DisclosureDatabase Number 564025.

Ex. LOGP_NEUTRAL LOGP_HCOOH I-1 3.77 3.86 Example 1: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.544 (6.4); 8.335 (3.9); 8.314 (4.1); 7.568 (2.9); 7.563(3.5); 7.534 (2.5); 7.529 (1.9); 7.513 (2.3); 7.508 (1.9); 3.323 (17.6);2.671 (0.3); 2.631 (16.0); 2.524 (1.1); 2.511 (19.3); 2.507 (38.0);2.502 (49.6); 2.498 (35.5); 2.493 (16.9); 2.075 (0.5); 0.008 (0.9);0.000 (21.7); −0.008 (0.7) I-2 3.48 3.52 Example 2: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.283 (3.7); 8.960 (2.3); 8.958 (2.3); 8.334 (2.7); 8.328(4.1); 4.030 (16.0); 3.323 (69.7); 3.181 (1.1); 3.162 (3.6); 3.144(3.6); 3.126 (1.1); 2.891 (1.2); 2.731 (1.0); 2.676 (0.4); 2.671 (0.6);2.667 (0.4); 2.506 (64.4); 2.502 (83.6); 2.498 (61.3); 2.333 (0.4);2.329 (0.5); 2.324 (0.4); 1.234 (4.1); 1.215 (8.1); 1.197 (3.8); 0.008(0.6); 0.000 (17.0); −0.008 (0.7) I-3 3.16 3.22 Example 3: ¹H-NMR (400.0MHz, d₆-DMSO): δ = 9.290 (4.0); 8.947 (2.7); 8.316 (4.5); 8.267 (2.9);7.953 (0.4); 4.059 (16.0); 4.019 (0.7); 3.327 (63.2); 3.036 (0.3); 2.965(0.4); 2.892 (2.5); 2.882 (0.5); 2.870 (0.5); 2.732 (2.2); 2.673 (0.5);2.580 (15.1); 2.507 (59.9); 2.503 (71.6); 2.499 (52.5); 2.330 (0.5);2.078 (0.4); 1.234 (0.4); 0.000 (0.4) I-4 2.65 2.70 Example 4: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.833 (0.3); 9.210 (3.9); 8.226 (4.1); 8.082(0.6); 7.993 (0.5); 7.608 (1.3); 7.593 (1.5); 7.587 (1.6); 7.572 (1.4);7.411 (1.3); 7.405 (1.4); 7.386 (1.4); 7.380 (1.4); 7.244 (1.0); 7.238(0.9); 7.222 (1.6); 7.216 (1.5); 7.201 (0.8); 7.195 (0.7); 3.785 (16.0);3.325 (80.3); 2.875 (1.0); 2.863 (1.0); 2.671 (0.7); 2.667 (0.6); 2.506(76.1); 2.502 (99.5); 2.498 (78.2); 2.464 (2.7); 2.329 (0.6); 2.075(0.3); 0.000 (2.6) I-5 3.26 3.30 Example 5: ¹H-NMR (400.0 MHz, d₆-DMSO):δ = 9.249 (3.5); 8.267 (3.7); 7.787 (1.2); 7.778 (2.7); 7.768 (2.9);7.749 (2.1); 7.729 (0.7); 3.807 (16.0); 3.324 (21.7); 2.671 (0.4); 2.557(15.5); 2.524 (1.1); 2.511 (22.7); 2.507 (44.4); 2.502 (57.4); 2.498(41.7); 2.493 (20.4); 2.329 (0.4); 0.008 (2.1); 0.000 (52.3); −0.009(2.1) I-6 2.74 2.75 Example 6: ¹H-NMR (601.6 MHz, CD3CN): δ = 9.182(3.5); 7.526 (1.9); 7.523 (2.0); 7.459 (1.7); 7.445 (2.7); 7.403 (1.7);7.400 (1.6); 7.390 (1.1); 7.386 (1.0); 3.927 (0.3); 3.770 (16.0); 2.978(0.3); 2.494 (14.5); 2.222 (0.5); 2.152 (1.6); 1.966 (0.6); 1.958 (1.5);1.954 (1.8); 1.950 (9.9); 1.946 (17.5); 1.942 (25.9); 1.938 (17.6);1.934 (8.7); 1.387 (5.1); 1.269 (0.3); 1.212 (0.4); 0.005 (0.3); 0.000(11.9); −0.006 (0.4) I-7 2.67 2.72 Example 7: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.411 (2.3); 9.408 (2.3); 9.379 (3.9); 9.333 (0.4); 8.751(2.4); 8.746 (2.5); 8.460 (4.1); 8.316 (0.5); 7.903 (0.3); 4.391 (16.0);4.199 (1.2); 4.147 (0.5); 4.138 (0.4); 4.121 (0.8); 4.114 (0.6); 4.107(0.7); 4.100 (0.7); 4.088 (0.7); 4.068 (0.4); 3.976 (0.7); 3.854 (0.6);3.843 (0.6); 3.833 (0.7); 3.829 (0.7); 3.819 (0.8); 3.803 (0.5); 3.795(0.6); 3.556 (0.6); 3.543 (0.8); 3.531 (0.5); 3.523 (0.6); 3.518 (0.8);3.510 (0.9); 3.494 (1.8); 3.477 (0.8); 3.468 (0.8); 3.464 (0.6); 3.455(0.5); 3.443 (0.6); 3.429 (0.4); 3.325 (63.6); 3.260 (0.8); 3.257 (0.8);3.241 (2.2); 3.238 (2.3); 3.223 (2.3); 3.219 (2.3); 3.201 (0.9); 2.676(0.5); 2.671 (0.7); 2.667 (0.6); 2.524 (1.8); 2.511 (41.0); 2.506(84.3); 2.502 (113.7); 2.498 (86.8); 2.493 (45.8); 2.333 (0.5); 2.329(0.7); 2.324 (0.6); 1.252 (4.4); 1.233 (9.5); 1.214 (4.3); 0.146 (0.4);0.008 (2.7); 0.000 (79.8); −0.008 (4.6); −0.150 (0.4) I-8 3.46 3.54Example 8: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.390 (2.1); 9.387 (2.1);9.377 (3.6); 8.577 (2.1); 8.572 (2.2); 8.379 (3.7); 8.316 (0.6); 4.384(16.0); 4.362 (0.4); 3.802 (0.3); 3.785 (0.9); 3.767 (1.3); 3.750 (0.9);3.733 (0.4); 3.322 (86.4); 2.675 (1.0); 2.671 (1.4); 2.666 (1.0); 2.524(3.7); 2.511 (79.1); 2.506 (160.9); 2.502 (213.1); 2.497 (155.9); 2.493(76.9); 2.333 (1.0); 2.329 (1.4); 2.324 (1.0); 1.569 (6.3); 1.551 (6.2);0.906 (6.4); 0.889 (6.3); 0.146 (1.3); 0.008 (10.0); 0.000 (280.2);−0.008 (11.2); −0.150 (1.3) I-9 3.64 3.66 Example 9: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.544 (9.2); 8.314 (2.7); 8.311 (2.8); 8.294 (2.9); 8.291(2.8); 7.739 (1.1); 7.735 (1.2); 7.719 (2.5); 7.715 (2.1); 7.701 (2.2);7.697 (2.1); 7.646 (3.6); 7.627 (2.2); 7.464 (1.9); 7.462 (1.8); 7.444(3.0); 7.426 (1.6); 7.424 (1.5); 3.322 (31.6); 3.155 (1.9); 3.136 (6.3);3.118 (6.4); 3.100 (2.0); 2.676 (0.6); 2.671 (0.8); 2.666 (0.6); 2.541(0.6); 2.524 (2.7); 2.511 (49.3); 2.507 (97.6); 2.502 (126.8); 2.497(89.7); 2.493 (42.1); 2.333 (0.6); 2.329 (0.8); 2.324 (0.6); 2.075(0.3); 1.360 (7.3); 1.341 (16.0); 1.323 (7.0); 0.146 (0.3); 0.008 (3.4);0.000 (84.9); −0.009 (2.9); −0.150 (0.3) I-10 2.08 2.15 Example 10:¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.271 (3.7); 8.267 (3.9); 8.137 (2.9);8.132 (3.0); 7.975 (2.1); 7.954 (3.6); 7.900 (2.2); 7.895 (2.1); 7.880(1.3); 7.874 (1.3); 6.870 (0.3); 3.977 (15.9); 3.748 (0.9); 3.444 (0.8);3.327 (95.2); 2.967 (16.0); 2.676 (0.3); 2.671 (0.5); 2.667 (0.3); 2.525(1.4); 2.507 (54.5); 2.502 (70.2); 2.498 (50.6); 2.494 (24.6); 2.333(0.3); 2.329 (0.4); 2.184 (0.5); 1.355 (3.8); 1.298 (0.9); 1.259 (1.2);1.234 (0.6); 0.008 (2.1); 0.000 (54.1); −0.009 (2.3) I-11 2.34 2.39Example 11: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.279 (0.6); 9.262 (3.9);8.380 (0.5); 8.317 (0.5); 8.260 (4.2); 8.164 (2.8); 8.159 (3.4); 8.152(0.5); 8.115 (1.7); 8.110 (1.5); 8.095 (2.1); 8.089 (1.9); 7.937 (3.4);7.917 (3.0); 7.902 (0.8); 7.897 (0.9); 7.885 (0.5); 7.565 (0.4); 7.545(0.6); 5.757 (1.6); 3.770 (0.5); 3.747 (16.0); 3.621 (0.4); 3.592 (1.6);3.445 (15.1); 3.436 (2.1); 3.327 (141.8); 2.675 (0.9); 2.671 (1.2);2.667 (0.9); 2.524 (4.2); 2.506 (141.2); 2.502 (182.5); 2.498 (131.5);2.333 (0.8); 2.329 (1.1); 2.324 (0.8); 1.298 (0.8); 1.259 (1.1); 1.235(0.5); 1.166 (0.3); 0.008 (2.3); 0.000 (56.4); −0.008 (2.3) I-12 1.831.88 Example 12: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.272 (4.2); 8.266(4.5); 8.036 (1.3); 8.023 (1.4); 8.015 (1.6); 8.002 (1.5); 7.966 (1.4);7.959 (1.6); 7.944 (1.5); 7.937 (1.5); 7.706 (0.8); 7.699 (0.8); 7.685(1.5); 7.678 (1.5); 7.664 (0.8); 7.657 (0.7); 3.973 (16.0); 3.336(80.5); 2.958 (16.0); 2.678 (0.4); 2.549 (0.3); 2.509 (67.3); 2.337(0.4) I-13 2.34 2.44 Example 13: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.285(3.9); 8.280 (4.2); 8.088 (2.3); 8.066 (4.9); 8.060 (3.8); 8.009 (2.3);8.004 (2.0); 7.988 (1.4); 7.983 (1.3); 3.973 (16.0); 3.327 (56.5); 3.313(1.6); 3.294 (1.2); 3.279 (1.2); 3.261 (1.1); 3.242 (0.3); 2.905 (1.1);2.886 (1.2); 2.871 (1.0); 2.853 (1.0); 2.671 (0.4); 2.507 (41.3); 2.502(56.0); 2.498 (43.9); 2.329 (0.4); 1.150 (3.8); 1.132 (8.2); 1.113(3.7); 0.000 (2.5) I-14 2.63 2.67 Example 14: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.289 (3.7); 8.430 (1.3); 8.412 (5.2); 8.288 (3.9); 8.287(3.9); 8.180 (1.6); 8.159 (1.4); 3.772 (16.0); 3.493 (14.4); 3.324(34.4); 2.524 (0.9); 2.511 (17.9); 2.506 (36.4); 2.502 (48.8); 2.497(36.6); 2.493 (18.8); 0.008 (1.9); 0.000 (52.6); −0.008 (2.6) I-15 1.921.95 Example 15: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.295 (3.5); 9.139(1.7); 9.135 (1.9); 9.127 (1.9); 9.123 (1.8); 8.579 (1.7); 8.575 (1.8);8.559 (1.9); 8.555 (1.8); 8.300 (3.6); 8.298 (3.7); 8.021 (1.9); 8.009(1.8); 8.001 (1.7); 7.989 (1.7); 3.867 (16.0); 3.794 (1.0); 3.775 (3.5);3.757 (3.5); 3.738 (1.0); 3.327 (10.2); 2.526 (0.5); 2.521 (0.7); 2.512(10.8); 2.508 (22.2); 2.503 (29.5); 2.499 (21.4); 2.494 (10.4); 1.209(3.6); 1.191 (7.9); 1.172 (3.5); 0.008 (1.8); 0.000 (50.2); −0.009 (1.9)I-16 3.21 3.26 Example 16: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.588 (2.0);9.585 (2.1); 9.314 (3.5); 8.780 (2.2); 8.776 (2.2); 8.331 (3.7); 8.316(0.4); 4.409 (0.3); 4.392 (1.0); 4.375 (1.4); 4.357 (1.0); 4.340 (0.3);3.914 (16.0); 3.322 (36.9); 2.676 (0.6); 2.671 (0.8); 2.667 (0.6); 2.524(2.0); 2.520 (3.2); 2.511 (42.6); 2.507 (88.2); 2.502 (118.2); 2.497(86.9); 2.493 (42.9); 2.333 (0.5); 2.329 (0.7); 2.324 (0.6); 1.260(13.3); 1.243 (13.2); 0.146 (0.8); 0.008 (6.7); 0.000 (191.2); −0.009(7.6); −0.150 (0.8) I-17 2.87 2.94 Example 17: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.204 (3.8); 8.228 (4.1); 7.627 (3.7); 7.618 (4.2); 7.536(1.5); 7.517 (2.1); 7.433 (0.9); 7.422 (1.2); 7.413 (1.2); 7.403 (1.1);7.392 (0.6); 3.768 (16.0); 3.327 (67.1); 2.986 (1.3); 2.968 (4.1); 2.950(4.1); 2.931 (1.4); 2.671 (0.5); 2.667 (0.3); 2.507 (57.2); 2.503(74.4); 2.498 (54.2); 2.334 (0.3); 2.329 (0.5); 2.325 (0.4); 1.180(4.3); 1.161 (8.7); 1.143 (4.1); 0.146 (0.5); 0.008 (3.9); 0.000 (88.8);−0.007 (3.9); −0.150 (0.5) I-18 2.11 2.13 Example 18: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.255 (3.5); 8.253 (3.7); 8.251 (3.6); 8.156 (1.3); 8.153(1.3); 8.138 (1.8); 8.134 (1.6); 8.020 (0.4); 8.017 (0.5); 8.002 (1.4);7.998 (1.4); 7.984 (1.6); 7.979 (1.5); 7.976 (1.4); 7.971 (1.6); 7.957(1.5); 7.953 (1.5); 7.938 (0.6); 7.934 (0.5); 7.878 (1.7); 7.875 (1.8);7.860 (1.2); 7.857 (1.2); 3.728 (16.0); 3.526 (0.5); 3.509 (1.3); 3.490(1.3); 3.473 (0.5); 3.330 (61.8); 2.671 (0.4); 2.525 (1.2); 2.511(25.5); 2.507 (50.6); 2.502 (65.3); 2.498 (46.3); 2.493 (21.9); 2.329(0.4); 1.119 (3.5); 1.101 (7.8); 1.082 (3.4); 0.008 (0.6); 0.000 (15.4);−0.009 (0.6) I-19 3.38 3.43 Example 19: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =9.226 (3.9); 8.243 (4.1); 7.705 (0.9); 7.699 (1.3); 7.684 (1.6); 7.678(2.9); 7.667 (3.6); 7.662 (2.3); 7.640 (3.4); 7.619 (1.8); 3.788 (16.0);3.323 (25.4); 2.999 (1.2); 2.981 (4.0); 2.963 (4.1); 2.944 (1.3); 2.671(0.4); 2.626 (0.3); 2.507 (47.1); 2.502 (61.4); 2.498 (45.8); 2.329(0.4); 2.300 (0.5); 1.177 (4.3); 1.159 (8.9); 1.140 (4.1); 0.008 (1.9);0.000 (45.5) I-20 2.05 2.08 Example 20: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =9.258 (4.1); 8.253 (4.3); 7.997 (1.5); 7.990 (2.5); 7.976 (2.4); 7.969(3.3); 7.956 (1.7); 7.918 (1.1); 7.911 (0.9); 7.897 (1.6); 7.890 (1.4);7.876 (0.7); 7.869 (0.6); 3.739 (16.0); 3.430 (15.0); 3.326 (81.6);2.671 (0.7); 2.666 (0.6); 2.506 (84.7); 2.502 (108.3); 2.498 (84.4);2.328 (0.7); 2.325 (0.5); 0.146 (0.6); 0.000 (128.1); −0.150 (0.6) I-212.93 2.98 Example 21: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.586 (2.4);9.583 (2.5); 9.317 (4.1); 8.798 (2.5); 8.794 (2.6); 8.341 (4.3); 3.925(16.0); 3.912 (1.3); 3.893 (3.6); 3.874 (3.7); 3.856 (1.1); 3.324(30.3); 2.671 (0.5); 2.506 (56.1); 2.502 (72.8); 2.498 (55.3); 2.329(0.5); 1.258 (3.8); 1.239 (8.2); 1.221 (3.7); 0.146 (0.4); 0.007 (3.2);0.000 (79.6); −0.150 (0.4) I-22 1.87 1.90 Example 22: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.261 (3.9); 8.261 (4.1); 8.107 (1.6); 8.087 (2.0); 7.942(0.8); 7.940 (1.0); 7.921 (1.7); 7.904 (2.1); 7.901 (2.4); 7.885 (2.2);7.820 (1.2); 7.818 (1.3); 7.801 (1.6); 7.799 (1.6); 7.783 (0.6); 7.780(0.7); 5.757 (1.1); 3.946 (16.0); 3.728 (0.5); 3.328 (59.2); 3.305(1.0); 3.286 (1.1); 3.272 (1.1); 3.253 (1.1); 2.885 (1.1); 2.867 (1.2);2.852 (1.0); 2.833 (1.0); 2.672 (0.3); 2.507 (37.2); 2.502 (48.9); 2.498(35.7); 1.149 (3.9); 1.130 (8.2); 1.112 (3.7); 1.102 (0.4); 0.007 (1.5);0.000 (35.2); −0.008 (1.5) I-23 3.96 4.02 Example 23: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.288 (4.1); 8.977 (2.7); 8.456 (2.7); 8.327 (4.3); 8.317(0.4); 4.033 (16.0); 3.395 (2.0); 3.377 (2.7); 3.357 (2.4); 3.327(77.5); 2.720 (2.3); 2.701 (2.8); 2.682 (2.2); 2.672 (0.7); 2.579 (1.5);2.560 (4.6); 2.542 (4.9); 2.523 (3.2); 2.507 (65.1); 2.502 (87.7); 2.498(70.2); 2.329 (0.6); 2.075 (0.9); 1.233 (0.6); 1.152 (4.7); 1.133 (9.3);1.115 (4.4); 0.000 (3.7) I-24 2.32 2.39 Example 24: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.241 (3.7); 8.588 (1.6); 8.585 (1.8); 8.577 (1.7); 8.574(1.8); 8.279 (3.8); 8.090 (1.5); 8.087 (1.6); 8.069 (1.7); 8.066 (1.8);7.638 (1.6); 7.627 (1.6); 7.618 (1.5); 7.606 (1.5); 3.975 (16.0); 3.324(34.0); 3.041 (1.1); 3.022 (3.7); 3.004 (3.8); 2.986 (1.2); 2.672 (0.3);2.525 (0.8); 2.507 (40.5); 2.503 (55.3); 2.498 (43.4); 2.329 (0.4);1.218 (4.0); 1.199 (8.3); 1.181 (3.9); 0.008 (1.5); 0.000 (45.1) I-252.97 3.08 Example 25: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.217 (3.6);8.235 (3.9); 7.564 (2.9); 7.560 (3.0); 7.555 (3.0); 7.544 (3.5); 7.460(2.0); 7.455 (1.8); 7.440 (1.4); 7.435 (1.3); 3.791 (16.0); 3.323(28.6); 2.671 (0.3); 2.506 (48.4); 2.502 (56.6); 2.498 (37.8); 2.329(0.4); 1.398 (0.8); 0.008 (2.5); 0.000 (64.5); −0.008 (2.5) I-26 2.762.81 Example 26: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.389 (2.0); 9.386(2.0); 9.366 (3.5); 8.849 (2.2); 8.845 (2.1); 8.370 (3.7); 6.870 (0.5);5.756 (0.4); 4.452 (0.5); 4.347 (15.7); 4.018 (0.6); 3.995 (0.4); 3.326(80.4); 3.151 (16.0); 2.676 (0.4); 2.671 (0.5); 2.667 (0.3); 2.524(1.2); 2.511 (28.7); 2.507 (56.3); 2.502 (72.6); 2.498 (52.3); 2.494(25.3); 2.334 (0.4); 2.329 (0.5); 2.325 (0.3); 2.183 (0.8); 1.355 (5.8);1.233 (0.6); 0.008 (1.2); 0.000 (33.6); −0.009 (1.3) I-27 1.84 1.87Example 27: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.253 (3.5); 8.275 (3.8);8.273 (3.7); 8.257 (1.5); 8.254 (1.4); 8.237 (1.8); 8.234 (1.7); 8.038(0.5); 8.035 (0.6); 8.020 (1.5); 8.016 (1.6); 8.001 (1.5); 7.998 (1.3);7.984 (1.2); 7.980 (1.4); 7.965 (1.6); 7.961 (1.7); 7.946 (0.7); 7.942(0.6); 7.903 (0.9); 7.895 (2.1); 7.892 (2.0); 7.877 (1.4); 7.873 (1.3);7.567 (0.4); 7.547 (0.6); 5.756 (8.2); 5.231 (0.7); 5.226 (0.6); 5.216(0.5); 5.211 (1.3); 5.205 (0.5); 5.196 (0.7); 5.190 (0.8); 5.175 (0.4);4.802 (2.1); 4.783 (4.1); 4.763 (2.6); 4.673 (2.9); 4.657 (3.1); 4.639(2.0); 3.746 (16.0); 3.732 (0.5); 3.602 (0.5); 3.594 (0.5); 3.325(51.0); 2.676 (0.3); 2.671 (0.4); 2.524 (1.2); 2.511 (26.7); 2.507(53.3); 2.502 (69.4); 2.498 (49.5); 2.493 (23.4); 2.333 (0.3); 2.329(0.5); 1.760 (0.5); 1.236 (0.7); 1.190 (0.3); 0.000 (2.3) I-28 3.22 3.29Example 28: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.561 (4.9); 8.983 (2.2);8.362 (2.2); 8.359 (2.2); 4.075 (16.0); 4.032 (0.3); 4.022 (0.4); 3.323(56.4); 3.202 (1.1); 3.184 (3.5); 3.165 (3.5); 3.147 (1.1); 2.676 (0.4);2.671 (0.6); 2.667 (0.4); 2.511 (33.1); 2.507 (65.1); 2.502 (84.7);2.498 (61.6); 2.494 (30.1); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4); 1.355(0.7); 1.252 (4.0); 1.233 (8.3); 1.215 (3.7); 0.008 (2.6); 0.000 (63.4);−0.008 (2.5) I-29 2.93 3.04 Example 29: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =9.302 (3.5); 8.962 (1.6); 8.959 (1.8); 8.951 (1.8); 8.947 (1.8); 8.457(1.3); 8.437 (1.4); 8.334 (3.7); 7.856 (1.7); 7.845 (1.7); 7.836 (1.6);7.824 (1.6); 4.092 (16.0); 3.329 (37.7); 2.526 (0.6); 2.512 (14.7);2.508 (30.1); 2.504 (40.6); 2.499 (31.1); 2.495 (16.5); 0.000 (1.9) I-302.36 2.41 Example 30: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.307 (3.8);8.443 (2.9); 8.305 (4.0); 8.190 (6.5); 4.008 (15.9); 3.327 (62.6); 2.995(16.0); 2.676 (0.4); 2.671 (0.5); 2.667 (0.4); 2.511 (28.7); 2.507(57.0); 2.502 (75.3); 2.498 (56.9); 2.334 (0.4); 2.329 (0.5); 2.325(0.4); 0.000 (3.6) I-31 3.86 3.94 Example 31: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.283 (3.4); 8.955 (2.1); 8.952 (2.1); 8.347 (2.1); 8.343(2.2); 8.334 (3.8); 4.021 (16.0); 3.324 (17.5); 3.137 (2.1); 3.119(3.6); 3.101 (2.2); 2.892 (1.6); 2.732 (1.3); 2.672 (0.4); 2.525 (0.7);2.512 (20.3); 2.507 (42.4); 2.503 (57.6); 2.498 (43.7); 2.494 (22.9);2.329 (0.4); 1.607 (1.2); 1.588 (2.4); 1.570 (2.5); 1.552 (1.4); 0.961(4.2); 0.943 (8.6); 0.924 (3.8); 0.008 (1.3); 0.000 (42.0); −0.009 (2.2)I-32 3.32 3.37 Example 32: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.580 (2.3);9.577 (2.3); 9.316 (3.9); 8.796 (2.4); 8.792 (2.4); 8.350 (4.1); 7.903(0.5); 7.898 (0.5); 7.547 (0.5); 5.756 (2.2); 3.923 (16.0); 3.898 (2.3);3.883 (1.8); 3.878 (2.4); 3.873 (1.8); 3.859 (2.3); 3.775 (0.8); 3.323(27.3); 2.676 (0.3); 2.671 (0.5); 2.667 (0.3); 2.524 (1.0); 2.511(25.7); 2.507 (52.2); 2.502 (69.6); 2.498 (51.6); 2.493 (26.0); 2.329(0.4); 2.324 (0.3); 1.737 (1.1); 1.718 (1.9); 1.699 (2.0); 1.680 (1.2);1.013 (4.1); 1.002 (0.9); 0.995 (8.4); 0.976 (3.8); 0.000 (9.4); −0.008(0.4) I-33 2.11 2.12 Example 33: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.315(3.7); 8.969 (1.6); 8.966 (1.8); 8.958 (1.8); 8.954 (1.7); 8.556 (1.6);8.552 (1.7); 8.536 (1.8); 8.532 (1.7); 8.319 (4.0); 7.938 (1.7); 7.926(1.6); 7.918 (1.6); 7.906 (1.5); 4.318 (16.0); 3.552 (0.9); 3.533 (1.0);3.519 (1.1); 3.500 (1.1); 3.481 (0.3); 3.324 (25.2); 3.031 (1.1); 3.012(1.2); 2.998 (1.0); 2.979 (1.0); 2.507 (37.9); 2.503 (49.7); 2.499(37.5); 1.303 (3.8); 1.285 (8.0); 1.266 (3.7); 0.000 (5.3) I-34 4.414.38 Example 34: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.332 (3.7); 8.517(4.3); 8.515 (4.4); 8.272 (3.7); 8.251 (3.9); 7.627 (0.5); 7.623 (0.6);7.614 (0.4); 7.597 (0.5); 7.575 (0.4); 7.566 (0.4); 7.556 (0.4); 7.542(2.9); 7.538 (3.4); 7.509 (2.4); 7.504 (1.7); 7.488 (2.1); 7.483 (1.8);3.321 (35.3); 2.680 (0.4); 2.675 (0.9); 2.671 (1.2); 2.666 (0.8); 2.662(0.4); 2.610 (16.0); 2.524 (3.5); 2.511 (65.6); 2.506 (129.9); 2.502(168.9); 2.497 (120.0); 2.493 (56.5); 2.337 (0.4); 2.333 (0.8); 2.329(1.1); 2.324 (0.8); 2.320 (0.4); 1.355 (1.2); 1.328 (0.4); 1.207 (0.3);1.189 (0.7); 1.168 (2.5); 1.160 (2.3); 1.145 (0.4); 1.058 (0.5); 0.146(0.4); 0.008 (3.6); 0.000 (97.2); −0.009 (3.2); −0.150 (0.4) I-35 4.074.03 Example 35: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.334 (5.6); 8.540(6.8); 8.538 (6.7); 8.234 (2.7); 8.231 (2.8); 8.214 (3.0); 8.211 (2.8);7.693 (1.0); 7.690 (1.0); 7.673 (2.6); 7.669 (2.1); 7.655 (2.3); 7.651(2.2); 7.621 (3.9); 7.602 (2.0); 7.440 (1.8); 7.437 (1.8); 7.420 (3.0);7.402 (1.5); 7.399 (1.4); 3.323 (126.5); 3.130 (2.0); 3.112 (6.6); 3.093(6.7); 3.075 (2.1); 2.680 (0.5); 2.675 (1.1); 2.671 (1.5); 2.666 (1.1);2.662 (0.5); 2.524 (4.8); 2.511 (84.8); 2.506 (166.1); 2.502 (215.2);2.497 (153.7); 2.493 (72.9); 2.333 (1.0); 2.329 (1.4); 2.324 (1.0);1.333 (7.5); 1.315 (16.0); 1.297 (7.2); 0.008 (1.0); 0.000 (28.0);−0.009 (0.9) I-36 2.64 2.67 Example 36: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =9.577 (2.7); 9.575 (2.7); 9.320 (4.2); 8.825 (2.8); 8.822 (2.8); 8.347(4.5); 7.902 (0.7); 7.897 (0.7); 7.886 (0.4); 7.566 (0.3); 7.546 (0.5);5.757 (1.3); 4.018 (1.1); 3.934 (16.0); 3.700 (15.4); 3.325 (73.6);2.671 (0.7); 2.506 (74.4); 2.502 (95.9); 2.498 (76.5); 2.328 (0.6);1.258 (0.3); 1.236 (1.0); 1.169 (0.8); 0.000 (2.4) I-37 3.10 3.17Example 37: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.392 (2.2); 9.388 (2.3);9.369 (3.8); 8.726 (2.3); 8.721 (2.4); 8.385 (3.9); 8.316 (0.5); 4.362(16.0); 3.627 (0.9); 3.608 (1.1); 3.594 (1.1); 3.575 (1.0); 3.324(136.2); 3.117 (1.0); 3.098 (1.2); 3.084 (1.0); 3.065 (0.9); 2.676(0.8); 2.671 (1.1); 2.667 (0.9); 2.507 (127.4); 2.502 (169.6); 2.498(129.7); 2.333 (0.8); 2.329 (1.1); 2.325 (0.9); 1.330 (3.8); 1.312(8.1); 1.293 (3.6); 0.146 (0.9); 0.008 (7.7); 0.000 (196.4); −0.150(0.9) I-38 2.63 2.68 Example 38: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.273(3.9); 8.266 (4.2); 8.141 (2.4); 8.120 (3.8); 8.105 (2.9); 8.100 (3.4);8.055 (2.4); 8.049 (2.0); 8.033 (1.5); 8.028 (1.3); 7.904 (0.8); 7.899(0.7); 7.894 (0.5); 7.887 (0.5); 7.697 (0.3); 7.568 (0.5); 7.548 (0.8);7.528 (0.3); 3.763 (16.0); 3.530 (0.6); 3.513 (1.3); 3.495 (1.4); 3.476(0.6); 3.357 (0.5); 3.328 (61.7); 2.676 (0.4); 2.671 (0.5); 2.667 (0.4);2.525 (1.3); 2.507 (57.0); 2.502 (75.7); 2.498 (56.3); 2.333 (0.3);2.329 (0.5); 2.325 (0.3); 1.125 (3.8); 1.107 (8.1); 1.088 (3.6); 0.000(0.6) I-39 3.45 3.52 Example 39: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.386(2.2); 9.383 (2.3); 9.374 (3.8); 8.774 (2.3); 8.769 (2.3); 8.316 (0.4);8.302 (3.8); 5.756 (0.4); 4.362 (16.0); 3.637 (0.5); 3.616 (0.9); 3.605(0.6); 3.596 (0.6); 3.585 (1.0); 3.564 (0.6); 3.322 (68.3); 2.993 (0.6);2.981 (0.7); 2.973 (0.7); 2.961 (1.1); 2.949 (0.7); 2.941 (0.7); 2.928(0.6); 2.676 (0.6); 2.671 (0.8); 2.666 (0.6); 2.511 (49.6); 2.506(97.4); 2.502 (127.7); 2.497 (95.5); 2.493 (49.9); 2.333 (0.6); 2.329(0.8); 2.324 (0.6); 2.029 (0.5); 2.010 (0.7); 1.994 (0.8); 1.975 (0.7);1.956 (0.4); 1.804 (0.4); 1.789 (0.6); 1.783 (0.5); 1.770 (0.6); 1.757(0.4); 1.754 (0.4); 1.146 (3.8); 1.128 (8.0); 1.109 (3.6); 0.146 (0.8);0.008 (8.1); 0.000 (174.8); −0.008 (10.0); −0.150 (0.8) I-40 3.10 3.15Example 40: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.347 (4.8); 8.561 (5.7);8.293 (2.2); 8.291 (2.3); 8.274 (2.4); 8.271 (2.3); 7.668 (1.0); 7.665(1.1); 7.647 (2.2); 7.630 (1.4); 7.627 (1.3); 7.480 (1.7); 7.460 (2.8);7.442 (1.3); 7.179 (2.9); 7.159 (2.6); 6.870 (1.5); 6.647 (0.8); 5.165(3.3); 5.147 (6.3); 5.130 (3.6); 4.804 (0.5); 4.788 (1.2); 4.771 (1.9);4.755 (1.2); 4.738 (0.4); 4.512 (3.8); 4.496 (6.3); 4.480 (3.3); 3.328(53.8); 2.672 (0.6); 2.507 (73.4); 2.503 (93.5); 2.499 (70.8); 2.330(0.6); 2.183 (2.4); 1.355 (16.0); 1.233 (0.9); 1.182 (0.6); 0.008 (3.2);0.000 (57.9) I-41 3.73 3.80 Example 41: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =9.277 (3.9); 8.989 (2.5); 8.456 (2.5); 8.453 (2.5); 8.345 (0.3); 8.333(4.2); 7.954 (0.5); 4.021 (0.4); 4.003 (1.1); 3.988 (16.0); 3.949 (0.4);3.932 (1.0); 3.916 (1.4); 3.899 (1.1); 3.883 (0.4); 3.325 (35.1); 2.892(3.7); 2.732 (3.3); 2.672 (0.3); 2.507 (40.5); 2.503 (53.7); 2.499(41.6); 2.330 (0.4); 1.235 (14.8); 1.219 (14.7); 0.008 (1.4); 0.000(30.8) I-42 3.39 3.46 Example I-42: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =9.881 (0.4); 9.213 (3.4); 8.238 (3.6); 8.236 (3.6); 8.136 (0.4); 8.085(0.7); 7.683 (0.3); 7.639 (2.8); 7.634 (2.9); 7.572 (2.4); 7.552 (3.7);7.504 (0.5); 7.499 (0.5); 7.483 (2.1); 7.478 (2.0); 7.462 (1.4); 7.457(1.3); 6.870 (0.4); 3.779 (16.0); 3.618 (0.4); 3.608 (0.3); 3.602 (1.0);3.585 (0.4); 3.325 (20.2); 3.098 (0.6); 3.067 (1.2); 3.048 (3.9); 3.030(4.0); 3.016 (0.9); 3.012 (1.3); 2.877 (1.1); 2.865 (1.1); 2.676 (0.4);2.671 (0.5); 2.667 (0.4); 2.525 (1.4); 2.520 (2.1); 2.511 (30.1); 2.507(61.5); 2.502 (81.2); 2.498 (58.8); 2.493 (28.4); 2.333 (0.4); 2.329(0.5); 2.324 (0.4); 2.183 (0.7); 1.776 (0.4); 1.769 (0.4); 1.760 (1.2);1.752 (0.4); 1.744 (0.4); 1.355 (5.3); 1.245 (0.8); 1.236 (0.4); 1.226(1.7); 1.218 (0.5); 1.208 (0.8); 1.193 (4.1); 1.175 (8.7); 1.156 (3.9);0.146 (0.4); 0.008 (2.9); 0.000 (88.8); −0.009 (3.1); −0.150 (0.4) I-432.61 2.69 Example I-43: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.259 (3.8);8.259 (4.0); 8.123 (6.1); 8.118 (3.1); 8.107 (2.5); 8.102 (1.5); 7.945(2.9); 7.939 (0.8); 7.929 (0.7); 7.923 (2.3); 5.757 (11.4); 3.742(16.0); 3.600 (0.7); 3.581 (2.2); 3.563 (2.2); 3.545 (0.7); 3.329(38.9); 2.671 (0.4); 2.525 (1.2); 2.511 (23.7); 2.507 (48.0); 2.502(63.6); 2.498 (47.5); 2.494 (24.1); 2.329 (0.4); 1.146 (3.7); 1.128(8.2); 1.109 (3.6); 0.008 (0.3); 0.000 (9.3); −0.008 (0.4) I-44 2.362.45 Example I-44: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.270 (3.8); 8.317(0.5); 8.273 (4.1); 8.022 (2.9); 8.016 (3.1); 7.986 (2.2); 7.966 (3.6);7.905 (2.1); 7.899 (1.9); 7.884 (1.3); 7.879 (1.2); 3.969 (16.0); 3.377(1.0); 3.359 (1.3); 3.344 (1.9); 3.329 (150.3); 3.307 (0.6); 2.945(1.1); 2.927 (1.2); 2.912 (1.0); 2.893 (0.9); 2.676 (0.9); 2.671 (1.2);2.667 (0.9); 2.524 (3.1); 2.507 (141.2); 2.502 (185.0); 2.498 (135.5);2.333 (0.9); 2.329 (1.2); 2.325 (0.9); 1.179 (3.8); 1.160 (8.2); 1.142(3.7); 0.008 (2.3); 0.000 (70.9); −0.009 (2.6); −0.150 (0.3) I-45 2.53Example I-45: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.295 (3.9); 8.364 (3.2);8.342 (3.4); 8.292 (4.1); 7.347 (3.4); 7.325 (3.3); 4.015 (1.0); 3.987(16.0); 3.922 (15.6); 3.910 (1.3); 3.733 (1.0); 3.714 (3.4); 3.695(3.4); 3.677 (1.0); 3.506 (0.3); 3.331 (66.6); 2.672 (0.5); 2.668 (0.4);2.507 (58.9); 2.503 (75.4); 2.498 (56.9); 2.334 (0.4); 2.329 (0.5);2.325 (0.4); 2.087 (2.0); 1.234 (0.8); 1.203 (3.6); 1.185 (7.9); 1.166(3.5); 0.008 (2.1); 0.000 (43.3) I-46 2.92 2.98 Example I-46: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.269 (4.1); 8.592 (1.8); 8.590 (1.9); 8.581(1.9); 8.578 (1.8); 8.306 (4.3); 8.094 (1.7); 8.092 (1.7); 8.074 (1.9);8.071 (1.8); 7.955 (0.8); 7.642 (1.6); 7.631 (1.6); 7.622 (1.5); 7.610(1.5); 3.979 (16.0); 3.334 (9.6); 3.046 (1.2); 3.027 (3.8); 3.009 (3.9);2.991 (1.3); 2.893 (4.9); 2.734 (4.4); 2.509 (22.7); 2.505 (28.6); 2.501(21.4); 1.220 (4.2); 1.202 (8.6); 1.184 (4.1); 0.000 (4.6) I-47 4.024.10 Example I-47: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.308 (3.5); 8.964(2.1); 8.961 (2.1); 8.355 (3.9); 8.353 (3.9); 8.341 (2.2); 8.338 (2.2);8.317 (0.3); 4.030 (16.0); 3.328 (183.2); 3.184 (1.1); 3.165 (3.5);3.147 (3.6); 3.129 (1.1); 2.676 (0.8); 2.671 (1.1); 2.667 (0.8); 2.525(2.5); 2.520 (3.8); 2.511 (53.3); 2.507 (109.8); 2.502 (147.2); 2.498(110.1); 2.494 (55.4); 2.334 (0.7); 2.329 (1.0); 2.325 (0.7); 1.235(4.2); 1.217 (8.3); 1.198 (3.8); 0.146 (1.1); 0.008 (8.0); 0.000(229.8); −0.009 (9.5); −0.150 (1.1) I-48 2.64 2.70 Example I-48: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.337 (2.2); 9.324 (2.3); 9.295 (4.0); 8.366(2.9); 8.353 (2.8); 8.273 (4.3); 5.757 (0.8); 3.919 (16.0); 3.894 (0.7);3.879 (1.3); 3.862 (1.3); 3.327 (92.4); 2.676 (0.6); 2.671 (0.8); 2.667(0.6); 2.507 (88.5); 2.502 (113.9); 2.498 (86.6); 2.333 (0.6); 2.329(0.8); 2.325 (0.6); 1.243 (3.6); 1.224 (7.4); 1.206 (3.4); 0.146 (0.6);0.008 (6.3); 0.000 (128.4); −0.150 (0.6) I-49 1.99 2.05 Example I-49:¹H-NMR (400.0 MHz, d₆-DMSO): δ = 11.328 (3.1); 9.295 (4.3); 8.532 (1.7);8.509 (4.8); 8.487 (4.4); 8.465 (1.5); 8.318 (0.6); 8.304 (4.7); 3.876(16.0); 3.847 (0.7); 3.658 (1.1); 3.639 (3.5); 3.621 (3.5); 3.602 (1.1);3.331 (78.4); 2.892 (0.3); 2.676 (1.0); 2.672 (1.3); 2.668 (1.0); 2.565(0.4); 2.507 (157.3); 2.503 (200.0); 2.498 (150.8); 2.344 (0.8); 2.334(1.0); 2.329 (1.4); 2.169 (15.8); 1.989 (1.1); 1.234 (0.5); 1.184 (3.8);1.175 (1.3); 1.166 (8.3); 1.148 (3.7); 0.008 (0.9); 0.000 (19.7) I-502.27 2.39 Example I-50: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 10.770 (2.6);9.256 (3.9); 8.290 (1.9); 8.277 (4.3); 8.268 (2.5); 8.242 (0.7); 8.115(3.0); 8.093 (2.4); 8.063 (0.4); 4.456 (1.9); 4.038 (0.6); 4.020 (0.7);3.979 (16.0); 3.332 (83.1); 2.966 (1.2); 2.948 (4.0); 2.929 (4.1); 2.911(1.3); 2.676 (0.4); 2.672 (0.5); 2.668 (0.4); 2.507 (62.3); 2.503(81.2); 2.498 (61.4); 2.334 (0.4); 2.330 (0.5); 2.325 (0.4); 2.184(1.9); 2.119 (15.2); 1.989 (2.6); 1.193 (0.7); 1.172 (4.5); 1.154 (9.1);1.135 (4.2); 0.008 (2.6); 0.000 (55.6); −0.008 (3.1) I-51 2.48 ExampleI-51: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.259 (4.5); 9.210 (2.4); 9.198(2.5); 8.278 (4.7); 8.276 (4.8); 8.226 (3.2); 8.214 (3.1); 5.757 (2.5);3.965 (0.7); 3.946 (0.8); 3.932 (0.8); 3.920 (0.7); 3.914 (0.8); 3.795(16.0); 3.375 (0.6); 3.356 (0.8); 3.328 (59.8); 3.305 (0.3); 2.676(0.4); 2.672 (0.5); 2.667 (0.4); 2.525 (1.2); 2.511 (27.2); 2.507(56.1); 2.502 (75.0); 2.498 (55.5); 2.494 (27.5); 2.334 (0.4); 2.329(0.5); 2.325 (0.4); 1.264 (3.7); 1.245 (7.9); 1.227 (3.8); 0.008 (1.2);0.000 (39.0); −0.008 (1.4) I-52 2.51 2.61 Example I-52: ¹H-NMR (601.6MHz, CD3CN): δ = 9.321 (2.5); 8.780 (3.9); 8.736 (2.6); 7.746 (3.8);3.824 (1.3); 3.809 (16.0); 3.799 (3.9); 3.787 (1.3); 2.141 (2.3); 1.965(10.4); 1.957 (0.4); 1.944 (3.9); 1.940 (5.2); 1.937 (3.8); 1.933 (2.0);1.297 (3.8); 1.285 (7.6); 1.273 (3.7); 0.000 (3.3) I-53 3.12 ExampleI-53: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.242 (3.5); 8.270 (3.7); 8.119(0.4); 8.064 (2.9); 8.042 (3.1); 7.123 (3.3); 7.101 (3.1); 4.012 (16.0);3.959 (0.4); 3.909 (1.6); 3.899 (16.0); 3.332 (95.1); 2.942 (1.2); 2.923(3.9); 2.905 (3.9); 2.887 (1.3); 2.677 (0.4); 2.672 (0.6); 2.668 (0.4);2.525 (1.6); 2.511 (32.5); 2.507 (64.4); 2.503 (84.3); 2.499 (63.2);2.334 (0.4); 2.330 (0.6); 2.325 (0.4); 1.990 (0.8); 1.175 (0.5); 1.144(4.1); 1.126 (8.6); 1.107 (4.0); 0.008 (2.3); 0.000 (60.3); −0.008 (3.0)I-54 3.07 3.16 Example I-54: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.293(3.9); 8.987 (2.7); 8.490 (2.7); 8.335 (4.1); 5.757 (0.6); 4.713 (1.2);4.699 (2.4); 4.685 (1.2); 4.595 (1.1); 4.581 (2.3); 4.567 (1.3); 4.041(16.0); 3.581 (1.1); 3.567 (2.2); 3.553 (1.1); 3.521 (1.2); 3.507 (2.2);3.493 (1.1); 3.327 (105.4); 2.671 (0.8); 2.506 (88.1); 2.502 (120.1);2.498 (96.8); 2.333 (0.6); 2.329 (0.8); 1.234 (0.4); 0.146 (0.4); 0.008(2.7); 0.000 (84.4); −0.150 (0.4) I-55 3.01 3.12 Example I-55: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 8.956 (3.9); 8.953 (4.0); 8.942 (2.0); 8.940(2.0); 8.317 (2.1); 7.904 (3.7); 7.902 (3.7); 3.950 (16.0); 3.332(109.0); 3.172 (1.0); 3.154 (3.3); 3.135 (3.4); 3.117 (1.0); 2.676(0.3); 2.672 (0.5); 2.667 (0.4); 2.525 (1.2); 2.520 (1.8); 2.512 (26.2);2.507 (53.9); 2.503 (71.3); 2.498 (52.0); 2.494 (25.3); 2.334 (0.3);2.330 (0.5); 2.325 (0.4); 1.251 (0.5); 1.232 (5.1); 1.214 (7.9); 1.195(3.5); 1.103 (0.3); 0.000 (6.1) I-56 1.56 1.61 Example I-56: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.502 (3.9); 9.497 (3.4); 9.306 (4.1); 8.900(4.0); 8.895 (3.4); 8.645 (1.9); 8.322 (4.5); 8.057 (1.9); 3.892 (16.0);3.843 (1.3); 3.825 (3.8); 3.806 (3.7); 3.788 (1.1); 3.332 (180.7); 2.676(0.9); 2.672 (1.1); 2.667 (0.8); 2.507 (135.9); 2.503 (156.6); 2.498(111.5); 2.334 (0.9); 2.330 (1.0); 2.325 (0.7); 1.298 (0.5); 1.259(1.0); 1.235 (5.5); 1.217 (8.5); 1.198 (3.8); 0.000 (14.4); −0.062 (0.6)I-57 2.82 2.89 Example I-57: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.596(2.3); 9.593 (2.2); 9.330 (3.8); 9.320 (0.5); 8.830 (2.3); 8.826 (2.2);8.353 (4.1); 4.994 (1.0); 4.982 (1.5); 4.969 (1.1); 4.877 (1.0); 4.865(1.5); 4.852 (1.2); 4.493 (1.1); 4.480 (1.5); 4.468 (1.0); 4.427 (1.2);4.414 (1.5); 4.402 (1.0); 3.957 (16.0); 3.947 (1.6); 3.919 (0.4); 3.813(0.3); 3.328 (182.7); 2.676 (0.7); 2.671 (1.0); 2.667 (0.7); 2.663(0.4); 2.524 (3.6); 2.511 (61.5); 2.507 (120.1); 2.502 (156.5); 2.498(114.9); 2.493 (57.0); 2.333 (0.7); 2.329 (1.0); 2.325 (0.7); 2.074(0.5); 1.235 (0.6); 0.008 (2.3); 0.000 (63.1); −0.008 (2.5) I-58 2.19Example I-58: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.553 (2.2); 9.550 (2.2);9.320 (3.9); 8.786 (2.4); 8.781 (2.4); 8.336 (4.1); 5.755 (1.0); 5.119(1.2); 5.106 (2.9); 5.093 (1.3); 4.066 (1.6); 4.052 (3.3); 4.038 (2.1);3.919 (16.0); 3.869 (1.1); 3.855 (2.7); 3.842 (2.5); 3.828 (0.9); 3.400(0.4); 3.393 (0.4); 3.384 (0.5); 3.345 (268.1); 3.309 (0.6); 2.672(0.4); 2.526 (1.1); 2.512 (22.7); 2.508 (46.1); 2.503 (61.2); 2.499(45.2); 2.494 (22.6); 2.330 (0.4); 0.000 (0.6) I-59 2.31 2.41 ExampleI-59: ¹H-NMR (600.1 MHz, CD3CN): δ = 9.085 (2.6); 8.843 (1.4); 8.842(1.6); 8.840 (1.5); 8.333 (1.7); 8.331 (1.6); 8.165 (2.9); 5.447 (1.4);3.979 (16.0); 3.725 (0.9); 3.715 (2.8); 3.705 (2.9); 3.695 (1.0); 3.459(0.9); 3.449 (1.8); 3.439 (0.8); 3.177 (2.4); 3.167 (4.3); 3.157 (2.2);2.145 (5.7); 1.957 (0.5); 1.953 (0.6); 1.949 (3.0); 1.945 (5.2); 1.941(7.5); 1.937 (5.0); 1.933 (2.5) I-60 1.76 1.77 Example I-60: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.262 (4.0); 8.968 (3.2); 8.963 (3.3); 8.415(1.6); 8.354 (3.0); 8.350 (3.1); 8.303 (4.3); 7.862 (1.6); 4.008 (16.0);3.331 (33.2); 3.113 (1.1); 3.095 (3.7); 3.076 (3.8); 3.058 (1.2); 2.508(35.4); 2.504 (46.2); 2.499 (34.8); 1.246 (4.0); 1.228 (8.5); 1.209(3.9); 0.008 (1.7); 0.000 (46.1); −0.008 (2.2) I-61 2.63 2.71 ExampleI-61: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.343 (3.7); 8.973 (1.6); 8.969(1.8); 8.961 (1.8); 8.957 (1.8); 8.559 (1.6); 8.555 (1.7); 8.539 (1.8);8.535 (1.8); 8.347 (4.0); 8.345 (4.0); 7.941 (1.7); 7.929 (1.6); 7.921(1.6); 7.909 (1.6); 4.320 (16.0); 3.561 (1.0); 3.542 (1.0); 3.528 (1.1);3.509 (1.1); 3.490 (0.3); 3.330 (33.2); 3.048 (1.1); 3.030 (1.2); 3.015(1.0); 2.997 (1.0); 2.677 (0.4); 2.672 (0.5); 2.668 (0.4); 2.525 (1.3);2.507 (56.6); 2.503 (75.2); 2.499 (56.4); 2.334 (0.4); 2.330 (0.5);2.325 (0.4); 1.301 (3.8); 1.282 (8.2); 1.264 (3.7); 0.146 (0.5); 0.008(4.0); 0.000 (110.8); −0.008 (5.6); −0.150 (0.5) I-62 2.15 2.17 ExampleI-62: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.207 (3.4); 8.318 (0.5); 8.194(3.7); 8.192 (3.6); 8.062 (1.6); 8.059 (1.7); 8.042 (2.2); 8.039 (2.2);7.947 (1.8); 7.928 (2.7); 7.908 (1.6); 7.735 (2.0); 7.732 (2.1); 7.716(1.8); 7.713 (1.7); 3.742 (16.0); 3.593 (1.0); 3.574 (3.5); 3.556 (3.6);3.537 (1.2); 3.329 (74.8); 2.676 (0.7); 2.671 (0.9); 2.667 (0.7); 2.662(0.4); 2.525 (2.4); 2.520 (3.6); 2.511 (50.5); 2.507 (105.6); 2.502(140.5); 2.498 (101.4); 2.493 (48.8); 2.334 (0.6); 2.329 (0.9); 2.324(0.6); 2.086 (0.7); 1.235 (1.3); 1.184 (4.0); 1.166 (9.0); 1.147 (3.9);1.140 (0.6); 0.146 (0.7); 0.008 (5.0); 0.000 (161.5); −0.009 (5.9);−0.150 (0.7) I-63 3.62 3.75 Example I-63: ¹H-NMR (400.0 MHz, d₆-DMSO): δ= 9.396 (5.6); 8.728 (2.2); 8.723 (2.3); 8.416 (4.1); 8.414 (3.9); 8.318(0.5); 4.362 (16.0); 3.635 (0.9); 3.617 (1.0); 3.602 (1.1); 3.583 (1.0);3.332 (165.3); 3.134 (1.0); 3.116 (1.2); 3.101 (1.0); 3.083 (1.0); 2.676(0.8); 2.672 (1.1); 2.667 (0.8); 2.525 (2.6); 2.511 (62.1); 2.507(126.3); 2.503 (165.5); 2.498 (121.7); 2.494 (60.8); 2.334 (0.8); 2.329(1.1); 2.325 (0.8); 1.327 (3.7); 1.308 (8.1); 1.290 (3.6); 0.146 (0.4);0.008 (3.1); 0.000 (96.0); −0.008 (4.1); −0.150 (0.4) I-64 3.95 3.93Example I-64: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.275 (2.6); 9.271 (2.5);8.943 (4.3); 8.584 (2.6); 8.580 (2.6); 8.318 (0.5); 7.701 (3.0); 7.680(3.9); 7.548 (3.8); 7.527 (3.0); 7.410 (4.6); 3.890 (16.0); 3.329(75.4); 3.140 (1.3); 3.122 (4.2); 3.104 (4.3); 3.086 (1.4); 2.676 (0.9);2.671 (1.2); 2.667 (0.9); 2.507 (140.3); 2.502 (179.9); 2.498 (134.5);2.334 (0.9); 2.329 (1.2); 2.325 (0.9); 1.281 (4.6); 1.263 (9.7); 1.245(4.5); 0.146 (0.4); 0.008 (3.6); 0.000 (84.0); −0.150 (0.4) I-65 4.314.37 Example I-65: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.217 (3.1); 9.076(4.1); 9.074 (4.1); 8.959 (2.3); 8.956 (2.3); 8.334 (2.3); 8.318 (1.7);8.288 (3.7); 8.211 (4.1); 8.209 (4.1); 5.758 (1.1); 4.005 (16.0); 3.328(226.4); 3.189 (1.1); 3.171 (3.5); 3.153 (3.6); 3.134 (1.1); 2.676(2.7); 2.671 (3.8); 2.667 (2.8); 2.525 (9.3); 2.520 (14.6); 2.511(211.4); 2.507 (434.4); 2.502 (573.8); 2.498 (421.2); 2.493 (209.9);2.333 (2.7); 2.329 (3.7); 2.324 (2.8); 1.258 (0.3); 1.243 (4.1); 1.225(8.8); 1.206 (3.9); 1.148 (0.3); 0.146 (1.3); 0.008 (9.7); 0.000(308.8); −0.008 (13.1); −0.150 (1.4) I-66 3.42 3.50 Example I-66: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.243 (3.5); 8.317 (0.4); 8.274 (3.7); 8.069(2.9); 8.047 (3.1); 7.116 (3.3); 7.094 (3.2); 4.017 (0.4); 4.000 (16.0);3.893 (15.8); 3.329 (74.5); 2.884 (2.3); 2.867 (3.7); 2.848 (2.4); 2.676(0.7); 2.671 (0.9); 2.667 (0.7); 2.525 (2.3); 2.511 (50.8); 2.507(105.0); 2.502 (139.6); 2.498 (102.9); 2.494 (51.4); 2.334 (0.6); 2.329(0.9); 2.325 (0.7); 1.496 (1.2); 1.478 (2.4); 1.460 (2.5); 1.442 (1.4);0.875 (4.2); 0.857 (8.4); 0.838 (3.7); 0.008 (0.8); 0.000 (28.2); −0.008(1.2) I-67 2.70 2.75 Example I-67: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =10.028 (0.5); 9.850 (0.4); 9.268 (0.7); 9.248 (3.0); 8.317 (1.0); 8.302(0.7); 8.262 (3.1); 8.236 (0.6); 8.194 (0.5); 8.119 (1.3); 8.097 (0.7);8.026 (2.6); 8.004 (2.6); 7.996 (0.5); 7.978 (0.6); 7.181 (0.8); 7.159(0.6); 7.133 (2.8); 7.111 (2.7); 4.442 (2.5); 4.071 (13.8); 4.017 (3.3);4.014 (3.6); 3.959 (1.9); 3.910 (16.0); 3.329 (346.6); 2.881 (1.4);2.869 (1.4); 2.676 (1.7); 2.671 (2.3); 2.667 (1.7); 2.525 (5.8); 2.511(128.4); 2.507 (263.1); 2.502 (348.1); 2.498 (256.2); 2.494 (127.6);2.422 (14.2); 2.334 (1.7); 2.329 (2.3); 2.325 (1.7); 1.989 (0.9); 1.234(0.3); 1.175 (0.5); 0.146 (0.4); 0.008 (3.2); 0.000 (99.9); −0.008(3.8); −0.150 (0.5) I-68 2.46 2.50 Example I-68: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.319 (4.1); 9.142 (1.6); 9.139 (1.9); 9.130 (1.8); 9.126(1.9); 8.582 (1.6); 8.578 (1.8); 8.562 (1.9); 8.558 (1.9); 8.328 (4.3);8.024 (1.7); 8.012 (1.7); 8.003 (1.6); 7.991 (1.6); 3.870 (16.0); 3.802(1.0); 3.783 (3.5); 3.765 (3.6); 3.746 (1.1); 3.333 (44.0); 2.676 (0.3);2.672 (0.5); 2.668 (0.4); 2.507 (56.6); 2.503 (74.8); 2.499 (56.9);2.330 (0.5); 1.209 (3.7); 1.191 (8.1); 1.172 (3.6); 0.008 (1.1); 0.000(28.7) I-69 4.32 4.37 Example I-69: ¹H-NMR (400.0 MHz, d₆-DMSO): δ =9.080 (4.3); 9.078 (4.2); 8.959 (2.4); 8.956 (2.4); 8.873 (1.8); 8.871(2.0); 8.867 (2.1); 8.865 (1.8); 8.337 (2.4); 8.334 (2.4); 8.181 (4.2);8.180 (4.2); 7.062 (2.5); 7.056 (2.5); 4.007 (16.0); 3.330 (22.5); 3.189(1.1); 3.170 (3.7); 3.152 (3.7); 3.133 (1.2); 2.677 (0.3); 2.672 (0.5);2.668 (0.3); 2.526 (1.2); 2.512 (26.3); 2.508 (53.3); 2.503 (70.1);2.499 (51.8); 2.495 (26.3); 2.330 (0.4); 2.326 (0.3); 2.077 (0.6); 1.244(4.0); 1.225 (8.7); 1.207 (3.9); 0.008 (1.3); 0.000 (37.3); −0.008 (1.8)I-70 3.24 3.29 Example I-70: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.272(4.0); 9.057 (2.0); 9.044 (2.1); 8.309 (4.2); 8.135 (2.8); 8.122 (2.7);4.021 (0.4); 3.846 (16.0); 3.328 (22.9); 2.736 (1.1); 2.717 (3.4); 2.699(3.5); 2.680 (1.3); 2.507 (37.7); 2.503 (49.4); 2.499 (37.9); 1.990(1.3); 1.397 (1.1); 1.193 (0.3); 1.176 (0.7); 1.158 (0.4); 0.985 (4.0);0.966 (8.1); 0.948 (3.8); 0.008 (1.7); 0.000 (44.7); −0.008 (2.1) I-712.93 Example I-71: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.293 (4.1); 8.368(3.1); 8.345 (3.3); 8.299 (4.3); 7.342 (3.4); 7.320 (3.2); 5.758 (0.9);4.017 (0.4); 3.985 (16.0); 3.918 (15.5); 3.716 (2.2); 3.701 (1.9); 3.696(2.5); 3.692 (1.8); 3.677 (2.2); 3.330 (25.0); 2.676 (0.4); 2.672 (0.5);2.668 (0.4); 2.507 (54.4); 2.503 (69.4); 2.499 (51.7); 2.330 (0.5);2.326 (0.3); 1.668 (1.1); 1.649 (2.0); 1.630 (2.0); 1.611 (1.2); 1.235(0.7); 0.993 (4.1); 0.974 (8.2); 0.956 (3.7); 0.000 (2.4) I-72 2.26 2.32Example I-72: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.581 (3.0); 9.576 (3.0);9.312 (4.1); 9.070 (3.3); 9.065 (3.2); 8.716 (1.0); 8.704 (0.9); 8.335(4.3); 8.091 (0.4); 7.660 (0.6); 7.645 (0.8); 7.641 (0.7); 7.626 (0.6);3.916 (16.0); 3.872 (1.3); 3.854 (3.8); 3.835 (3.9); 3.817 (1.4); 3.736(0.6); 3.694 (0.7); 3.626 (0.8); 3.613 (0.8); 2.671 (1.0); 2.506(105.6); 2.502 (135.4); 2.498 (103.6); 2.333 (0.7); 2.329 (0.9); 1.989(0.7); 1.298 (0.6); 1.252 (4.0); 1.234 (9.7); 1.215 (3.9); 1.193 (0.3);1.175 (0.5); 0.000 (3.0) I-73 2.20 2.25 Example I-73: ¹H-NMR (400.0 MHz,d₆-DMSO): δ = 9.297 (3.6); 9.268 (0.9); 9.255 (0.6); 9.208 (0.4); 8.404(3.2); 8.382 (3.4); 8.317 (0.4); 8.298 (3.9); 8.238 (0.6); 8.119 (0.8);8.106 (0.4); 8.097 (0.9); 8.084 (0.4); 8.024 (0.5); 8.022 (0.5); 7.996(0.4); 7.975 (0.4); 7.352 (3.6); 7.330 (3.5); 7.181 (0.8); 7.159 (0.8);7.087 (0.4); 7.069 (0.4); 7.067 (0.4); 5.758 (2.8); 4.564 (1.5); 4.442(3.0); 4.115 (0.7); 4.015 (4.7); 3.988 (16.0); 3.931 (15.4); 3.909(3.9); 3.568 (0.8); 3.544 (14.4); 3.331 (131.8); 2.676 (0.7); 2.672(0.9); 2.667 (0.7); 2.525 (2.7); 2.511 (52.5); 2.507 (106.0); 2.503(139.4); 2.498 (102.4); 2.494 (51.6); 2.334 (0.6); 2.329 (0.9); 2.325(0.7); 1.259 (0.5); 1.234 (1.5); 0.000 (5.6) I-74 3.36 3.49 ExampleI-74: ¹H-NMR (601.6 MHz, CD3CN): δ = 8.905 (3.0); 8.903 (3.0); 8.852(1.6); 8.850 (1.6); 8.500 (1.9); 8.313 (1.5); 8.311 (2.1); 8.309 (1.4);8.183 (1.7); 8.181 (1.7); 7.962 (3.4); 7.961 (3.4); 4.001 (16.0); 3.940(0.4); 3.124 (1.1); 3.111 (3.4); 3.099 (3.5); 3.087 (1.2); 2.639 (0.7);2.184 (55.7); 2.109 (1.2); 2.005 (2.2); 1.998 (195.7); 1.989 (2.7);1.985 (1.8); 1.981 (10.0); 1.977 (18.2); 1.973 (26.5); 1.969 (18.0);1.965 (9.0); 1.882 (1.2); 1.419 (0.4); 1.404 (0.7); 1.373 (0.6); 1.330(4.1); 1.318 (9.0); 1.309 (1.6); 1.305 (5.2); 1.301 (3.4); 0.914 (0.6)I-75 2.84 2.94 Example I-75: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.582(2.6); 9.107 (4.5); 8.797 (2.6); 8.794 (2.8); 8.761 (3.5); 8.668 (2.9);8.361 (4.6); 8.314 (0.3); 5.754 (2.9); 3.939 (1.0); 3.920 (3.5); 3.897(16.0); 3.883 (1.4); 3.316 (65.0); 2.675 (0.8); 2.671 (1.1); 2.666(0.9); 2.506 (121.1); 2.502 (165.0); 2.497 (131.6); 2.333 (0.7); 2.328(1.1); 2.324 (0.9); 1.988 (0.8); 1.272 (3.7); 1.253 (8.2); 1.235 (4.5);1.175 (0.4); 0.146 (0.5); 0.008 (3.6); 0.000 (102.8); −0.150 (0.5) I-763.73 3.84 Example I-76: ¹H-NMR (601.6 MHz, CD3CN): δ = 9.334 (1.1);9.333 (1.2); 9.331 (1.2); 9.329 (1.1); 9.015 (1.4); 9.014 (1.7); 8.867(2.5); 8.865 (2.3); 8.751 (1.2); 8.750 (1.3); 8.747 (1.3); 8.287 (2.6);8.286 (2.3); 8.036 (1.9); 5.446 (0.6); 3.879 (0.9); 3.867 (16.0); 3.855(3.0); 3.842 (0.9); 2.129 (16.5); 1.964 (0.3); 1.955 (0.9); 1.951 (1.2);1.947 (9.5); 1.943 (17.4); 1.939 (24.5); 1.935 (16.4); 1.931 (8.6);1.313 (3.1); 1.300 (6.6); 1.288 (3.1); 1.270 (0.6); 0.005 (0.6); 0.000(19.1); −0.006 (0.7) I-77 3.81 3.90 Example I-77: ¹H-NMR (601.6 MHz,CD3CN): δ = 9.333 (1.3); 9.332 (1.5); 9.330 (1.5); 8.871 (3.2); 8.869(3.1); 8.750 (1.6); 8.748 (1.6); 8.736 (1.3); 8.734 (1.4); 8.731 (1.4);8.730 (1.2); 8.250 (3.0); 8.249 (3.0); 6.869 (1.7); 6.865 (1.7); 5.446(0.7); 3.884 (1.1); 3.871 (4.7); 3.869 (16.0); 3.859 (3.6); 3.847 (1.1);2.133 (5.1); 1.956 (0.3); 1.952 (0.4); 1.948 (3.5); 1.944 (6.3); 1.940(9.0); 1.936 (6.1); 1.932 (3.2); 1.314 (3.5); 1.302 (7.5); 1.290 (3.6);1.285 (0.4); 1.267 (0.5); 0.000 (5.6)

Use Examples

Ctenocephalides felis—in vitro Contact Test

For the coating of the test tubes, 9 mg of active ingredient are firstdissolved in 1 ml of acetone p.a. and then diluted to the desiredconcentration with acetone p.a. 250 μl of the solution are distributedhomogeneously on the inner walls and base of a 25 ml test tube byturning and rocking on an orbital shaker (rocking rotation at 30 rpm for2 h). With 900 ppm active ingredient solution and internal surface 44.7cm², given homogeneous distribution, an area-based dose of 5 μg/cm² isachieved.

After the solvent has evaporated off, the tubes are populated with 5-10adult cat fleas (Ctenocephalides felis), sealed with a perforatedplastic lid and incubated in a horizontal position at room temperatureand ambient humidity. After 48 h, efficacy is determined. To this end,the test tubes are stood upright and the fleas are knocked to the baseof the tube. Fleas which remain motionless at the base or move in anuncoordinated manner are considered to be dead or moribund.

A substance shows good efficacy against Ctenocephalides felis if atleast 80% efficacy was achieved in this test at an application rate of 5μg/cm². 100% efficacy means that all the fleas were dead or moribund. 0%efficacy means that no fleas were harmed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 5 μg/cm²:I-18, I-21

Boophilus microplus—Injection Test (BOOPMI Inj)

-   Solvent: dimethyl sulphoxide

To produce an appropriate active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of solvent and the concentrate isdiluted with solvent to the desired concentration.

1 μl of the active ingredient solution is injected into the abdomen of 5engorged adult female cattle ticks (Boophilus microplus). The animalsare transferred into dishes and kept in a climate-controlled room.

Efficacy is assessed after 7 days by laying of fertile eggs. Eggs whichare not visibly fertile are stored in a climate-controlled cabinet untilthe larvae hatch after about 42 days. An efficacy of 100% means thatnone of the ticks has laid any fertile eggs; 0% means that all the eggsare fertile.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 80% at an application rate of 20 μg/animal:I-21

Ctenocephalides felis—Oral Test (CTECFE)

-   Solvent: dimethyl sulphoxide

For the purpose of producing an appropriate active ingredientformulation, 10 mg of active ingredient are mixed with 0.5 ml ofdimethyl sulphoxide. Dilution with citrated cattle blood gives thedesired concentration.

About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with parafilm is placed onto thechamber. The cylinder contains the blood/active ingredient preparation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined. 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 ppm: I-21

Lucilia cuprina Test (LUCICU)

-   Solvent: dimethyl sulphoxide

To produce an appropriate active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) aretransferred into a test vessel containing minced horsemeat and theactive ingredient preparation of the desired concentration.

After 2 days, the kill in % is determined. 100% means that all thelarvae have been killed; 0% means that none of the larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm:I-18, I-21

Musca domestica Test (MUSCDO)

-   Solvent: dimethyl sulphoxide

To produce an appropriate active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with sugar solution and the activeingredient formulation of the desired concentration are populated with10 adult houseflies (Musca domestica).

After 2 days, the kill in % is determined. 100% means that all of theflies have been killed; 0% means that none of the flies have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 95% at an application rate of 20 ppm: I-21

Myzus persicae—Spray Test (MYZUPE)

-   Solvent: 78 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that none of the aphids have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:I-10, I-13, I-18, I-22, I-23, I-24, I-43, I-44, I-48, I-52

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha:I-4, I-12, I-14, I-17, I-18, I-19, I-21, I-38, I-42, I-45, I-46, I-49,I-50, I-51, I-56, I-61, I-68

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 g/ha: I-39

Phaedon cochleariae—Spray Test (PHAECO)

-   Solvent: 78.0 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active ingredient formulation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:I-2, I-3, I-4, I-5, I-10, I-12, I-13, I-14, I-18, I-19, I-21, I-22, I-24, I-25, I-26, I-28, I-29, I-31, I-36, I-37, I-38, I-39, I-41, I-42,I-43, I-44, I-45, I-46, I-47, I-48, I-49, I-50, I-51, I-52, I-53, I-54,I-55, I-61, I-68, I-73

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 500 g/ha:I-30, I-63

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-11

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 100 g/ha:I-17

Spodoptera frugiperda—Spray Test (SPODFR)

-   Solvent: 78.0 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water.

Leaf discs of maize (Zea mays) are sprayed with an active ingredientformulation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all thecaterpillars have been killed; 0% means that no caterpillars have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:I-2, I-21, I-26, I-37, I-39, I-42, I-46, I-47, I-54, I-61, I-63, I-68

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 500 g/ha:I-14, I-19, I-48

Tetranychus urticae—Spray Test, OP-Resistant (TETRUR)

-   Solvent: 78.0 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested by all stages of thegreenhouse red spider mite (Tetranychus urticae) are sprayed with anactive ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that none of the spider miteshave been killed.

In this test, for example, the following compound from the preparationexamples shows an efficacy of 100% at an application rate of 500 g/ha:I-68

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha:I-2, I-13, I-19, I-22, I-28, I-42, I-44, I-53

In this test, for example, the following compound from the preparationexamples shows an efficacy of 90% at an application rate of 100 g/ha:I-48

Myzus persicae—Spray Test (MYZUPE)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water. If the addition of ammonium salts or/andpenetrants is required, these are each added in a concentration of 1000ppm to the formulation solution.

Bell pepper plants (Capsicum annuum) heavily infested by the green peachaphid (Myzus persicae) are treated by spraying with the activeingredient formulation in the desired concentration.

After 6 days, the kill in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compound from the preparationexamples shows an efficacy of 97% at an application rate of 100 ppm:I-11

Meloidogyne incognita Test

-   Solvent: 125.0 parts by weight of acetone

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is mixed with the stated amount of solvent and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active ingredient solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compound from the preparationexamples shows an efficacy of 100% at an application rate of 20 ppm:I-68

Comparative Examples:

Myzus persicae—Contact Test (MYZUPE c)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water. In the event that addition of ammoniumsalts or/and penetrants (rapeseed oil methyl ester) is required, theseare each pipetted in a concentration of 1000 ppm after the finishedformulation solution has been diluted.

One-leaved bell pepper plants (Capsicum annuum) heavily infested by thegreen peach aphid (Myzus persicae) are treated by spraying the undersideof the leaf with the active ingredient formulation in the desiredconcentration.

After the desired time, the kill in % is determined. 100% means that allthe aphids have been killed and 0% means that none of the aphids havebeen killed.

In this test, for example, the following compound from the preparationexamples shows good efficacy compared to the known compound fromWO2013018928 (see table):

Myzus persicae—Translaminar Test (MYZUPE t)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water. In the event that addition of ammoniumsalts or/and penetrants (rapeseed oil methyl ester) is required, theseare each pipetted in in a concentration of 1000 ppm after the finishedformulation solution has been diluted.

One-leaved bell pepper plants (Capsicum annuum) heavily infested by thegreen peach aphid (Myzus persicae) are treated by spraying the top sideof the leaf with the active ingredient formulation in the desiredconcentration.

After the desired time, the kill in % is determined. 100% means that allthe aphids have been killed and 0% means that none of the aphids havebeen killed.

In this test, for example, the following compound from the preparationexamples shows good efficacy compared to the known compound fromWO2013018928 (see table):

Aphis gossypii—Contact Test (APHIGO c)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water. In the event that addition of ammoniumsalts or/and penetrants (rapeseed oil methyl ester) is required, theseare each pipetted in a concentration of 1000 ppm after the finishedformulation solution has been diluted.

One-leaved cotton plants (Gossypium hirsutum) heavily infested by thecotton aphid (Aphis gossypii) are treated by spraying the underside ofthe leaf with the active ingredient formulation in the desiredconcentration.

After the desired time, the kill in % is determined. 100% means that allthe aphids have been killed and 0% means that none of the aphids havebeen killed.

In this test, for example, the following compound from the preparationexamples shows good efficacy compared to the known compound fromWO2013018928 (see table):

Aphis gossypii—Translaminar Test (APHIGO t)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water. In the event that addition of ammoniumsalts or/and penetrants (rapeseed oil methyl ester) is required, theseare each pipetted in in a concentration of 1000 ppm after the finishedformulation solution has been diluted.

One-leaved cotton plants (Gossypium hirsutum) heavily infested by thecotton aphid (Aphis gossypii) are treated by spraying the top side ofthe leaf with the active ingredient formulation in the desiredconcentration.

After the desired time, the kill in % is determined. 100% means that allthe aphids have been killed and 0% means that none of the aphids havebeen killed.

In this test, for example, the following compound from the preparationexamples shows good efficacy compared to the known compound fromWO2013018928 (see table):

Nephotettix cincticeps Test (NEPHCI)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water. In the event that addition of ammoniumsalts or/and penetrants (rapeseed oil methyl ester) is required, theseare each pipetted in in a concentration of 1000 ppm after the finishedformulation solution has been diluted.

Rice plants (Oryza sativa, var. Balilla) are treated by spraying withthe active ingredient formulation in the desired concentration and thenpopulated with larvae of the green rice leafhopper (Nephotettixcincticeps).

After the desired time, the kill in % is determined. 100% means that allleafhoppers have been killed; 0% means that none of the leafhoppers havebeen killed.

In this test, for example, the following compound from the preparationexamples shows good efficacy compared to the known compound fromWO2013018928 (see table):

Nilaparvata lugens Test (NILALU)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active ingredient formulation, 1 part byweight of active ingredient is dissolved using the stated parts byweight of solvent and made up with water containing an emulsifierconcentration of 1000 ppm until the desired concentration is attained.To produce further test concentrations, the preparation is diluted withemulsifier-containing water. In the event that addition of ammoniumsalts or/and penetrants (rapeseed oil methyl ester) is required, theseare each pipetted in in a concentration of 1000 ppm after the finishedformulation solution has been diluted.

Rice plants (Oryza sativa, var. Balilla) are treated by spraying withthe active ingredient formulation in the desired concentration and thenpopulated with L3 larvae of the brown planthopper (Nilaparvata lugens).

After the desired time, the feeding damage in % is determined. 100%means that no feeding damage is found; 0% means that the feeding damageto the treated plant corresponds to that of the untreated control.

In this test, for example, the following compound from the preparationexamples shows good efficacy compared to the known compound fromWO2013018928 (see table):

Animal Substance Structure species Concentration % efficacy dat* Ex.I-21

MYZUPE c MYZUPE t MYZUPE t APHIGO c APHIGO t NEPHCI NEPHCI NEPHCI NILALUNILALU  2.4 g/ha   12 g/ha  2.4 g/ha  2.4 g/ha  2.4 g/ha 0.16 ppm 0.16ppm 0.16 ppm   4 ppm   4 ppm 85 98 90 98 65 90 95 100  90 100  14 dat 14dat 14 dat  7 dat  7 dat 14 dat 21 dat 34 dat 21 dat 28 dat Ex. 5 knownfrom WO2013018928

MYZUPE c MYZUPE t MYZUPE t APHIGO c APHIGO t NEPHCI NEPHCI NEPHCI NILALUNILALU  2.4 g/ha   12 g/ha  2.4 g/ha  2.4 g/ha  2.4 g/ha 0.16 ppm 0.16ppm 0.16 ppm   4 ppm   4 ppm 50  0  0 15  0  0  0  0 35 20 14 dat 14 dat14 dat  7 dat  7 dat 14 dat 21 dat 34 dat 21 dat 28 dat *dat = daysafter treatment (days)

The invention claimed is:
 1. A compound of formula (I)

in which A¹ is nitrogen, A² is —N—R⁵, A³ is oxygen, A⁴ is ═C—R⁴, A⁵ is═C—H, R¹ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, amino, (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonylamino,aminosulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,di(C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl, or is (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, eachof which is optionally mono- or polysubstituted identically ordifferently by aryl, hetaryl or heterocyclyl, where aryl, hetaryl orheterocyclyl may each independently optionally be mono- orpolysubstituted identically or differently by halogen, cyano, nitro,hydroxyl, amino, carboxyl, carbamoyl, aminosulphonyl, (C₁-C₆)alkyl,(C₃-C₆)cycloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy,(C₁-C₆)alkylthio, (C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphimino, (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulphoximino,(C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl or benzyl, or R¹ is aryl,hetaryl or heterocyclyl, each of which is optionally mono- orpolysubstituted identically or differently by halogen, cyano, nitro,hydroxyl, amino, carboxyl, carbamoyl, (C₁-C₆)alkyl, (C₃-C₈)cycloalkyl,(C₁-C₆)-alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy,(C₁-C₆)alkylthio,(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphimino, (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulphoximino,(C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl, (═O) (only in the case ofheterocyclyl) or (═O)₂ (only in the case of heterocyclyl), R^(2a),R^(2b), R³ and R⁴ are each independently hydrogen, cyano, halogen,nitro, acetyl, hydroxyl, amino, SCN, tri-(C₁-C₆)alkylsilyl,(C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,(C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alkylaminosulphonyl,(C₁-C₆)alkylsulphoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino),or R^(2a), R^(2b), R³, R⁴ are each independently aryl or hetaryl, eachof which is optionally mono- or polysubstituted identically ordifferently, where (in the case of hetaryl) at least one carbonyl groupmay optionally be present and/or where possible substituents in eachcase are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl,amino, SCN, tri-(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,(C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alkylaminosulphonyl,(C₁-C₆)alkylsulphoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, R⁵ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or(C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl, n is 0, 1 or 2, with the provisothat the compound of formula (I) is not a compound in which thevariables are defined as follows: A¹ A² A³ A⁴ A⁵ N N-methyl O ═C—H ═C—HN N-methyl O ═C—H ═C—H N N-methyl O ═C—H ═C—H N N-methyl O ═C—H ═C—H NN-methyl O ═C—H ═C—H R¹ n R³ R^(2a) R^(2b) C₂H₅ 2 CF₃ H H C₂H₅ 2 CF₃ CF₃H CH₃ 2 CF₃ CF₃ H C₂H₅ 2 CF₃ OCHF₂ H C₂H₅ 2 Br CF₃  H.


2. The compound of formula (I) according to claim 1 in which A¹ isnitrogen, A² is —N—R⁵, A³ is oxygen, A⁴ is ═C—R⁴, A⁵ is ═C—H, R¹ is(C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonylamino,(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonylamino, or is(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl,(C₃-C₆)cycloalkyl, each of which is optionally mono- or disubstitutedidentically or differently by aryl, hetaryl or heterocyclyl, where aryl,hetaryl and heterocyclyl may each optionally be mono- or disubstitutedidentically or differently by halogen, cyano, carbamoyl, aminosulphonyl,(C₁-C₄)alkyl, (C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,(C₁-C₄)alkylsulphonyl, (C₁-C₄)alkylsulphimino, or R¹ is aryl, hetaryl orheterocyclyl, each of which is optionally mono- or disubstitutedidentically or differently by halogen, cyano, carbamoyl, (C₁-C₄)alkyl,(C₃-C₆)cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)alkylsulphimino, (C₁-C₄)alkylsulphoximino, (C₁-C₄)alkylcarbonyl,(C₃-C₄)trialkylsilyl, (═O) (only in the case of heterocyclyl) or (═O)₂(only in the case of heterocyclyl), R^(2a), R^(2b), R³ and R⁴ are eachindependently hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino,SCN, tri-(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulphonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,aminosulphonyl, (C₁-C₄)alkylaminosulphonyl,di(C₁-C₄)alkylaminosulphonyl, aminothiocarbonyl, NHCO—(C₁-C₄)alkyl((C₁-C₄)alkylcarbonylamino), or R^(2a), R^(2b), R³ and R⁴ are eachindependently phenyl or hetaryl, each of which is mono- or disubstitutedidentically or differently, where (in the case of hetaryl) at least onecarbonyl group may optionally be present and/or where possiblesubstituents in each case are as follows: cyano, halogen, nitro, acetyl,amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, aminosulphonyl,(C₁-C₄)alkylaminosulphonyl, di(C₁-C₄)alkylaminosulphonyl, R⁵ is(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)haloalkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulphinyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulphonyl-(C₁-C₄)alkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, n is 0, 1 or
 2. 3. The compound ofthe formula (I) according to claim 1 in which A¹ is nitrogen, A² is—N—R⁵, A³ is oxygen, A⁴ is ═C—R⁴, A⁵ is ═C—H, R¹ is (C₁-C₄)alkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,or is (C₁-C₄)alkyl optionally monosubstituted by phenyl, pyridyl,pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl, thiazolyl,tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl, where phenyl,pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl,thiazolyl, tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl may eachoptionally be mono- or disubstituted identically or differently byhalogen, (C₁-C₄)alkyl or (C₁-C₄)haloalkyl, or R¹ is phenyl, pyridyl,pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl, thiazolyl,tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl, each of which isoptionally mono- or disubstituted identically or differently by halogen,(C₁-C₄)alkyl or (C₁-C₄)haloalkyl, R^(2a) is hydrogen, cyano,aminocarbonyl, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,(C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulphinylor (C₁-C₄)haloalkylsulphonyl, R^(2b) is hydrogen, (C₁-C₄)alkoxy,(C₁-C₄)haloalkyl, NHCO—(C₁-C₄)alkyl or halogen, R³ is hydrogen, halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylthio,(C₁-C₄)haloalkylsulphinyl, (C₁-C₄)haloalkylsulphonyl, or is phenyl,pyrazolyl or imidazolyl, each of which is optionally monosubstituted bytrifluoromethyl, R⁴ is hydrogen, halogen, cyano or (C₁-C₃)alkyl, R⁵ is(C₁-C₄)alkyl or (C₁-C₄)alkoxy-(C₁-C₄)alkyl, n is 0, 1 or
 2. 4. Thecompound of the formula (I) according to claim 1 in which A¹ isnitrogen, A² is —N—R^(5,) A³ is oxygen, A⁴ is ═C—H, A⁵ is ═C—H, R¹ ismethyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl,tert-butyl, cyclobutyl, hydroxyethyl (—CH₂—CH₂—OH), fluoromethyl,difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, —(CH₂)₂—S—C₂H₅,—(CH₂)₂—SO₂—C₂H₅ or

R^(2a) is hydrogen, cyano, aminocarbonyl (CONH₂), fluoromethyl,difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio,trifluoromethylsulphonyl, trifluoromethylsulphinyl, fluorine orchlorine, R^(2b) is hydrogen, methoxy, ethoxy, trifluoromethyl,methylcarbonylamino (NHCO-methyl), fluorine or chlorine, R³ is fluorine,chlorine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,trifluoromethylthio, trifluoromethylsulphonyl, trifluoromethylsulphinyl,or is phenyl, pyrazol-1-yl or imidazol-1-yl, each of which is optionallymonosubstituted by trifluoromethyl, R⁴ is hydrogen, fluorine, chlorine,bromine or cyano, R⁵ is methyl, ethyl, i-propyl, methoxymethyl ormethoxyethyl, n is 0, 1 or
 2. 5. The compound of the formula (I)according to claim 1 in which A¹ is nitrogen (N), A² is —N—CH_(3,) A³ isoxygen, A⁴ is ═C—H, A⁵ is ═C—H, R¹ is methyl, ethyl, n-propyl, i-propyl,cyclopropyl, n-butyl, i-butyl, tert-butyl, cyclobutyl, hydroxyethyl(—CH₂—CH₂—OH), fluoromethyl, difluoromethyl, trifluoromethyl,fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,pentafluoroethyl, —(CH₂)₂—S—C₂H₅, —(CH₂)₂—SO₂—C₂H₅ or

 (oxetan-3-yl), R^(2a) is hydrogen, cyano, aminocarbonyl (CONH₂),fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphonyl,trifluoromethylsulphinyl, fluorine or chlorine, R^(2b) is hydrogen,methoxy, ethoxy, trifluoromethyl, methylcarbonylamino (NHCO-methyl),fluorine or chlorine, R³ is fluorine, chlorine, fluoromethyl,difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,trifluoromethylthio, trifluoromethylsulphonyl, trifluoromethylsulphinyl,or is phenyl,

 (pyrazol-1-yl) or

 (imidazol-1-yl), each of which is optionally monosubstituted bytrifluoromethyl, n is 0, 1 or
 2. 6. The compound of the formula (I)according to claim 1 in which A¹ is nitrogen (N), A² is —N—CH_(3,) A³ isoxygen, A⁴ is ═C—H, A⁵ is ═C—H, R¹ is methyl, ethyl, n-propyl, i-propyl,trifluoromethyl, —CH₂—CH₂—F, —CH₂—CH₂—OH, —(CH₂)₂—S—C₂H₅,—(CH₂)₂—SO₂—C₂H₅ or

R^(2a) is hydrogen, trifluoromethyl, cyano, CONH₂, fluorine or chlorine,R^(2b) is hydrogen, chlorine, trifluoromethyl, methoxy or NHCOCH₃, R³ ispentafluoroethyl, trifluoromethyl, chlorine, 4-CF₃(C₆H₄),4-(CF₃)pyrazol-1-yl, 3-(CF₃)pyrazol-1-yl or 4-(CF₃)imidazol-1-yl, n is0, 1 or
 2. 7. The compound of the formula (I) according to claim 1,wherein R^(2b) is acetyl, amino, SCN, tri-(C₁-C₆)alkylsilyl,(C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₂-C₆)alkenyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylsulphinyl, (C₁-C₆)haloalkylsulphinyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyloxy, (C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylthiocarbonyl, (C₁-C₆)haloalkylcarbonyl,(C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)alkylaminocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,di-(C₁-C₆)alkylaminothiocarbonyl, (C₂-C₆)alkenylaminocarbonyl,di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)cycloalkylaminocarbonyl,(C₁-C₆)alkylsulphonylamino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino,aminosulphonyl, (C₁-C₆)alkylaminosulphonyl,di-(C₁-C₆)alkylaminosulphonyl, (C₁-C₆)alkylsulphoximino,aminothiocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di-(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylamino,NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino), is in each caseoptionally singly or multiply, identically or differently substitutedhetaryl, where at least one carbonyl group may optionally be presentand/or where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri-(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,(C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulphonyl,(C₁-C₆)alkylaminosulphonyl, di-(C₁-C₆)alkylaminosulphonyl,(C₁-C₆)alkylsulphoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino.
 8. The compound of the formula (I) according toclaim 1, wherein R^(2b) is acetyl, amino, SCN, tri-(C₁-C₄)alkylsilyl,(C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkyl(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulphinyl,(C₁-C₄)haloalkylsulphinyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyloxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,aminothiocarbonyl, (C₁-C₄)alkylaminocarbonyl,di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,(C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulphonyl,(C₁-C₄)alkylaminosulphonyl, di-(C₁-C₄)alkylaminosulphonyl,aminothiocarbonyl, NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), is ineach case singly or doubly, identically or differently substitutedhetaryl, where at least one carbonyl group may optionally be presentand/or where possible substituents in each case are as follows: cyano,halogen, nitro, acetyl, amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)haloalkylsulphonyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulphonylamino,(C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulphonyl,(C₁-C₄)alkylaminosulphonyl, di-(C₁-C₄)alkylaminosulphonyl.
 9. Thecompound of the formula (I) according to claim 1, wherein R^(2b) is(C₁-C₄)alkoxy or NHCO—(C₁-C₄)alkyl.
 10. The compound of the formula (I)according to claim 1, wherein R^(2b) is methoxy, ethoxy or NHCO-methyl.11. The compound of the formula (I) according to claim 1, wherein R^(2b)is methoxy or NHCOCH₃.
 12. A composition comprising a content of atleast one compound of the formula (I) according to claim 1 and one ormore customary extenders and/or surfactants.
 13. A method forcontrolling pests, comprising allowing a compound of the formula (I)according to claim 1 to act on the pests and/or a habitat thereof.
 14. Acompound of the formula (I)

wherein A¹ is nitrogen, A² is N-methyl, A³ is oxygen, A⁴ is nitrogen, A⁵is CH, R¹ is C₂H₅, R^(2a) is CF₃, R^(2b) is H, R³ is CF₃, and n is 0.15. The compound of the formula (I) according to claim 1, wherein thevariables are defined as follows: A¹ A² A³ A⁴ A⁵ R¹ n R³ R^(2a) R^(2b) NN-methyl O CH CH —(CH₂)₂—SO₂—C₂H₅ 2 CF₃ CF₃ H N N-methyl O CH CH i-C₃H₇1 CF₃ CF₃ H N N-methyl O CH CH i-C₃H₇ 2 CF₃ CF₃ H N N-methyl O CH CH—(CH₂)₂—S—C₂H₅ 0 CF₃ CF₃ H N N-methyl O CH CH CF₃ 0 CF₃ H H N N-methyl OCH CH n-C₃H₇ 0 CF₃ CF₃ H N N-methyl O CH CH n-C₃H₇ 2 CF₃ CF₃ H NN-methyl O CH CH n-C₃H₇ 1 CF₃ CF₃ H N N-methyl O CH CH i-C₃H₇ 0 CF₃ CF₃H N N-methyl O CH CH C₂H₅ 2 CF₃ H 5-OMe N N-methyl O CH CH C₂H₅ 0 C₂F₅ HH N N-methyl O CH CH C₂H₅ 0 C₂F₅ CF₃ H N N-methyl O CH CH C₂H₅ 2 CF₃ H3-CF₃ N N-methyl O CH CH C₂H₅ 2 CF₃ H 5-NHCOMe N N-methyl O CH CH C₂H₅ 0CF₃ H 5-NHCOMe N N-methyl O CH CH C₂H₅ 1 CF₃ H 3-CF₃ N N-methyl O CH CHC₂H₅ 2 Cl CF₃ H N N-methyl O CH CH C₂H₅ 0 CF₃ H 5-OMe N N-methyl O CH CHCH₂—CH₂F 2 CF₃ CF₃ H N N-methyl O CH CH C₂H₅ 0 Cl CF₃ H N N-methyl O CHCH C₂H₅ 2 CF₃ CONH₂ H N N-methyl O CH CH CH₂—CH₂F 2 CF₃ CF₃ H N N-methylO CH CH CH₂—CH₂OH 2 CF₃ CF₃ H N N-methyl O CH CH CH₂—CH₂OH 0 CF₃ CF₃ H NN-methyl O CH CH C₂H₅ 0 CF₃ CONH₂ H N N-methyl O CH CH C₂H₅ 1 C₂F₅ H H NN-methyl O CH CH C₂H₅ 1 C₂F₅ CF₃ H N N-methyl O CH CH C₂H₅ 0 4-CF₃(C₆H₄)CF₃ H N N-methyl O CH CH C₂H₅ 0 4-(CF₃)pyrazol-1-y1 CF₃ H N N-methyl OCH CH n-C₃H₇ 0 CF₃ H 5-OMe N N-methyl O CH CH CH3 0 CF₃ H 5-OMe NN-methyl O CH CH C₂H₅ 2 C₂F₅ H H N N-methyl O CH CH C₂H₅ 03-(CF₃)pyrazol-1-y1 CF₃ H N N-methyl O CH CH C₂H₅ 0 CF₃ H 3-CF₃ NN-methyl O CH CH n-C₃H₇ 2 CF₃ H 5-OMe N N-methyl O CH CH C₂H₅ 2 CF₃ CN HN N-methyl O CH CH CH₃ 2 CF₃ H 5-OMe N N-methyl O CH CH C₂H₅ 04-(CF₃)imidazol-1-yl CF₃ H N N-methyl O CH CH C₂H₅ 24-(CF₃)imidazol-1-yl CF₃ H N N-methyl O CH CH C₂H₅ 2 4-(CF₃)pyrazol-1-y1CF₃ H N N-methyl O CH CH C₂H₅ 2 3-(CF₃)pyrazol-1-y1 CF₃  H.


16. The compound of the formula (I) according to claim 1, wherein thevariables are defined as follows: A¹ A² A³ A⁴ A⁵ N N-methyl O CH CH NN-methyl O CH CH N N-methyl O CH CH N N-methyl O CH CH N N-methyl O CHCH N N-methyl O CH CH N N-methyl O CH CH N N-methyl O CH CH N N-methyl OCH CH R¹ n R³ R^(2a) R^(2b) —(CH₂)₂—SO₂—C₂H₅ 2 CF₃ CF₃ H i-C₃H₇ 1 CF₃CF₃ H i-C₃H₇ 2 CF₃ CF₃ H —(CH₂)₂—S—C₂H₅ 0 CF₃ CF₃ H CF₃ 0 CF₃ H H n-C₃H₇0 CF₃ CF₃ H n-C₃H₇ 2 CF₃ CF₃ H n-C₃H₇ 1 CF₃ CF₃ H i-C₃H₇ 0 CF₃ CF₃  H.


17. The compound of the formula (I) according to claim 1, wherein thevariables are defined as follows: A¹ A² A³ A⁴ A⁵ R¹ n R³ R^(2a) R^(2b) NN-methyl O CH CH C₂H₅ 2 CF₃ H 5-OMe N N-methyl O CH CH C₂H₅ 0 C₂F₅ H H NN-methyl O CH CH C₂H₅ 0 C₂F₅ CF₃ H N N-methyl O CH CH C₂H₅ 2 CF₃ H 3-CF₃N N-methyl O CH CH C₂H₅ 2 CF₃ H 5-NHCOMe N N-methyl O CH CH C₂H₅ 0 CF₃ H5-NHCOMe N N-methyl O CH CH C₂H₅ 1 CF₃ H 3-CF₃ N N-methyl O CH CH C₂H₅ 2Cl CF₃ H N N-methyl O CH CH C₂H₅ 0 CF₃ H 5-OMe N N-methyl O CH CHCH₂—CH₂F 2 CF₃ CF₃ H N N-methyl O CH CH C₂H₅ 0 Cl CF₃ H N N-methyl O CHCH C₂H₅ 2 CF₃ CONH₂ H N N-methyl O CH CH CH₂—CH₂F 2 CF₃ CF₃ H N N-methylO CH CH CH₂—CH₂OH 2 CF₃ CF₃ H N N-methyl O CH CH CH₂—CH₂OH 0 CF₃ CF₃ H NN-methyl O CH CH C₂H₅ 0 CF₃ CONH₂ H N N-methyl O CH CH C₂H₅ 1 C₂F₅ H H NN-methyl O CH CH C₂H₅ 1 C₂F₅ CF₃ H N N-methyl O CH CH C₂H₅ 0 4-CF₃(C₆H₄)CF₃ H N N-methyl O CH CH C₂H₅ 0 4-(CF₃)pyrazol-1-y1 CF₃ H N N-methyl OCH CH n-C₃H₇ 0 CF₃ H 5-OMe N N-methyl O CH CH CH₃ 0 CF₃ H 5-OMe NN-methyl O CH CH C₂H₅ 2 C₂F₅ H H N N-methyl O CH CH C₂H₅ 03-(CF₃)pyrazol-1-y1 CF₃ H N N-methyl O CH CH C₂H₅ 0 CF₃ H 3-CF₃ NN-methyl O CH CH n-C₃H₇ 2 CF₃ H 5-OMe N N-methyl O CH CH C₂H₅ 2 CF₃ CN HN N-methyl O CH CH CH₃ 2 CF₃ H 5-OMe N N-methyl O CH CH C₂H₅ 04-(CF₃)imidazol-1-yl CF₃ H N N-methyl O CH CH C₂H₅ 24-(CF₃)imidazol-1-yl CF₃ H N N-methyl O CH CH C₂H₅ 2 4-(CF₃)pyrazol-1-y1CF₃ H N N-methyl O CH CH C₂H₅ 2 3-(CF₃)pyrazol-1-y1 CF₃  H.


18. The compound of the formula (I) according to claim 1 in which R¹ is(C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulphinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulphonyl-(C₁-C₄)alkyl,or is (C₁-C₄)alkyl monosubstituted by phenyl, pyridyl, pyrimidyl,pyridazinyl, pyrazinyl, pyrazolyl, triazolyl, thiazolyl, tetrazolyl,piperazinyl, tetrahydrofuryl or oxetanyl, where phenyl, pyridyl,pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, triazolyl, thiazolyl,tetrazolyl, piperazinyl, tetrahydrofuryl or oxetanyl may each optionallybe mono- or disubstituted identically or differently by halogen,(C₁-C₄)alkyl or (C₁-C₄)haloalkyl, or R¹ is phenyl, pyridyl, pyrimidyl,pyridazinyl, pyrazinyl, pyrazolyl, triazolyl, thiazolyl, tetrazolyl,piperazinyl, tetrahydrofuryl or oxetanyl, each of which is optionallymono- or disubstituted identically or differently by halogen,(C₁-C₄)alkyl or (C₁-C₄)haloalkyl.
 19. The compound of the formula (I)according to claim 1 in which R³ is hydrogen, (C₁-C₄)alkyl,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl,(C₁-C₄)alkylsulphonyl, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulphinyl,(C₁-C₄)haloalkylsulphonyl, or is phenyl, pyrazolyl or imidazolyl, eachof which is optionally monosubstituted by trifluoromethyl.
 20. Thecompound of the formula (I) according to claim 1 in which R^(2a) iscyano, aminocarbonyl, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulphinyl, (C₁-C₄)alkylsulphonyl,(C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulphinyl or(C₁-C₄)haloalkylsulphonyl.
 21. The compound of the formula (I) accordingto claim 1 in which R_(2b) is methoxy, ethoxy, trifluoromethyl,methylcarbonylamino (NHCO-methyl), fluorine or chlorine.
 22. A compoundof formula (I)

in which A¹ is nitrogen, A² is —N—R⁵, A³ is oxygen, A⁴ is ═C—R⁴, A⁵ is═C—H, R¹ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, amino, (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonylamino,aminosulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl,di(C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl, or is (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, eachof which is optionally mono- or polysubstituted identically ordifferently by aryl, hetaryl or heterocyclyl, where aryl, hetaryl orheterocyclyl may each independently optionally be mono- orpolysubstituted identically or differently by halogen, cyano, nitro,hydroxyl, amino, carboxyl, carbamoyl, aminosulphonyl, (C₁-C₆)alkyl,(C₃-C₆)cycloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy,(C₁-C₆)alkylthio, (C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphimino, (C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulphoximino,(C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl or benzyl, or R¹ is aryl,hetaryl or heterocyclyl, each of which is optionally mono- orpolysubstituted identically or differently by halogen, cyano, nitro,hydroxyl, amino, carboxyl, carbamoyl, (C₁-C₆)alkyl, (C₃-C₈)cycloalkyl,(C₁-C₆)-alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulphinyl, (C₁-C₆)alkylsulphonyl, (C₁-C₆)alkylsulphimino,(C₁-C₆)alkylsulphimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulphoximino,(C₁-C₆)alkylsulphoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl, (═O) (only in the case ofheterocyclyl) or (═O)₂ (only in the case of heterocyclyl), R_(2a),R^(2b), R³ and R⁴ are each independently hydrogen, cyano, halogen,nitro, acetyl, hydroxyl, amino, SCN, tri-(C₁-C₆)alkylsilyl,(C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,(C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alkylaminosulphonyl,(C₁-C₆)alkylsulphoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino),or R^(2a) , R^(2b), R³ and R⁴ are each independently aryl or hetaryl,each of which is optionally mono- or polysubstituted identically ordifferently, where (in the case of hetaryl) at least one carbonyl groupmay optionally be present and/or where possible substituents in eachcase are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl,amino, SCN, tri-(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl,(C₁-C₆)haloalkylsulphinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl,(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyl,(C₁-C₆)haloalkylsulphonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulphonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulphonyl,(C₁-C₆)alkylaminosulphonyl, di(C₁-C₆)alkylaminosulphonyl,(C₁-C₆)alkylsulphoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, R⁵ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl₄C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulphonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or(C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl, n is 0, 1 or 2, wherein when R³ isCF₃, R⁴ is H, R⁵ is CH₃, R^(2b) is H, and R¹ is CH₃ or CH₂CH₃, thenR^(2a) is not H, CF₃, Br, or Cl; and wherein when R³ is CF₃, R⁴ is H, R⁵is CH₃, R^(2b) is 3-CH₃, and R¹ is CH₂CH₃, then R^(2a) is not H, CF₃,Br, or Cl.